


SPNKINKBINGO 2016

by leatherwhiskeycoffeeplaid



Category: Supernatural, Supernatural RPF
Genre: Alcohol, Alpha/Beta/Omega Dynamics, Alpha/Omega, Anal Fingering, Anal Play, Anal Sex, Angelic Grace Kink (Supernatural), Angst, BDSM, Biting, Blindfolds, Cheating, Claiming, Claiming Bites, Cock Rings, Collars, Come Eating, Come Marking, Come Swallowing, Coming Untouched, Condoms, Cunnilingus, Daddy Kink, Dirty Talk, Dom/sub, Double Penetration, Dubious Consent, Exhibitionism, F/M, Fluff, Food Sex, Frottage, Gangbang, Guilty Pleasures, Hair-pulling, Handcuffs, Knotting, Lingerie, Masturbation, Mommy Kink, Multiple Orgasms, Nipple Clamps, Office Sex, Oral Fixation, Oral Sex, Orgasm Delay/Denial, Orgasm Denial, Pegging, Praise Kink, Pregnancy, Prostate Milking, Public Sex, Rimming, Rope Bondage, Secret Relationship, Sex Toys, Sexual Roleplay, Size Difference, Spanking, Spitroasting, Squirting, Strap-Ons, Teasing, Teen Pregnancy, Threesome - F/M/M, Triple Penetration, True Mates, Unplanned Pregnancy, Unsafe Sex, Vaginal Fingering, Vaginal Sex, Whipping, Wing Kink
Language: English
Status: Completed
Published: 2018-12-04
Updated: 2018-12-04
Packaged: 2019-09-06 23:56:22
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 23
Words: 29,509
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/16843012
Author URL: https://archiveofourown.org/users/leatherwhiskeycoffeeplaid/pseuds/leatherwhiskeycoffeeplaid
Summary: Collection of fics and aesthetics from tumblr's spnkinkbingo from 2016





	1. Shtuppin' the Nanny

**Author's Note:**

> After starting over the reader finds that her new male nanny is good at more than just helping take care of her son.

You knew starting over wasn’t going to be easy. From the divorce, to finding a good job that let you move as far from your ex as possible but still provide for your son. It was tough but you had managed to find a company in Kansas looking to hire, and you made the trek there with your 6 year old and started looking for a home as well as child care.

Your relator had been a wonderful woman named Mary, and she had found you a great little home not far outside the city. When you mentioned to her that your next step was to find child care for the summer months and after school, Mary was quick to give you the number to a nanny service her son worked for.

At first the thought of having a male nanny was a little strange, but after you spoke with the couple in charge, you were reassured that all those that worked for their company were fully trained in CPR, first aid, and had gotten degrees in early childhood development. These facts eased your worries, and appointments were made to find a right fit for you and your son.

They sent them over through the next few days. Most of them young women who were nice, but didn’t seem to click with your son, and the two older women that were sent just didn’t understand how you were raising your son to be so carefree about everything.

“Children need strict rules dear,” one had told you, and you just bit your tongue before showing her the door.

Finally you called to ask about maybe interviewing some men, and the first to show up was Sam Winchester, Mary’s boy. He was tall, ridiculously so, and he had long hair almost to his shoulders. He’d smiled wide when you opened the door, dimples forming on his face as you greeted him.

“Hi, I’m Sam Winchester. I think my mother sold you this house.”

You gave a soft laugh and felt your face start to heat up just looking at this man who was way too attractive to be a nanny. “She did and she’s the one that recommended you. Come on in and we can get this started.”

He followed you into your living room, your son Tommy sat off to the side playing with some toy cars on a road mapped carpet. The two of you took a seat on your sofa and you reached for your notebook full of questions for Sam.

It had started simple, where did he go to school, were his credentials up to date, what activities did he like doing with the kids, but when you asked about why he’d been let go from his last nanny job he blushed. His ears turning a bright pink and he bit the edge of his mouth, looking down at his large hands folded in his lap.

“That one is kind of hard to explain. The husband of the last family I worked for thought I was hitting on his wife. I wasn’t, but she was so he fired me. I don’t do very well with husbands or dads. The moms seem to like me, and so do the kids, but something about me makes the dads uneasy I guess.”

_‘It’s probably how fucking massive and gorgeous you are. I wonder if he’s trained in swimming. Maybe he can teach Tommy, with his shirt off.’_

“It’s okay. How are you with swimming? The house has a pool and Tommy loves the water.”

Sam smiled and you became transfixed by how his eyes seemed to glow with a mix of blues and greens.

“I love to swim. Had lessons as a kid and go every chance I get in the summer.”

_‘Fuck yes, I might catch him out there then.’_

“That is great. Just really great. Um, maybe you can spend some time with Tommy and see if he likes you.”

Sam gave you another wide grin and you had to remember to breath as he stood up and walked over to your son.

_‘Good lord he looks great from behind too. I wonder if everything about him is big? He’s got hands bigger than my head. I wonder if he can lift me?’_

The sound of your son laughing pulled you out of your thoughts, and you smiled as you watched him ram his tiny red car into the blue one Sam held in his hand.

It was decided then that Sam was just the right nanny for you and your son.

There was an adjustment period as Sam learned your routine, and you got used to having a man around the house again. The first time you had come home, finding Sam cooking dinner in your kitchen you almost jumped out of your skin. That is until you smelled the spaghetti sauce he was making.

Tommy loved having Sam around, and since it was summer you always heard about the day they had playing outside or splashing around in the pool. Oh how you wished you could be home when they were in the pool together, but you worked during the week. And on weekends Sam was free to do whatever he wanted.

A month and a half into Sam’s service as your nanny and you found yourself wishing you could stay home just once. With the fourth of July falling on a Monday you had the day off, and had asked Sam if he had any plans for the holiday.

“I usually just end up at my folks house, help my dad on the grill so he can spend time playing with my nieces.”

“Oh you never mentioned any other siblings. Your mom didn’t either.”

“Yeah, I got a brother Dean. He and his wife Cassie are one of those couples that break up and get back together all the time. If she didn’t mention him, it’s because they were off again. Mom gets mad at him when he and Cassie fight.”

You huffed a laugh and bit the corner of your lip. ‘Just ask him. Worse he can say is no.’

“Did you maybe want to spend it here with us? I was just gonna grill and let Tommy swim for a bit. Thought I might get some sparklers or something for him to celebrate with.”

Sam gave you one of his smiles that made his dimples deepen in his cheeks and he shook his head slightly to flip his hair out of his eyes. “I’d love to. That sounds like a lot of fun. Should I bring anything?”

_‘Should I tell him to bring beer? I don’t want him to think I’m an alcoholic or trashy. Wine, it’s classy.’_

“I don’t know if you drink, but if you do wine would be great.”

He nodded, “wine, sure. Any preferences? I’m usually just a beer kind of guy.”

You bit at your lip and laughed, “I have no idea. I don’t really drink wine. My ex liked to but beer is great. Please bring beer.”

Sam laughed along with you and you set the time for him to come over that Monday.

He had shown up around 2, a six pack of beer in his hand and dressed in a white v-neck and swim trunks. A shudder ran through your body as you realized you were going to see him in just those shorts, soaking wet.

“Thanks for coming Sam.” You held the door open and he walked in heading for your kitchen. “Your family wasn’t upset you were spending the holiday here?”

Sam pulled open your refrigerator and placed the bottles inside to keep cold. “No. They were fine with it. Actually my mother is hoping this means something more will be coming between the two of us.” He chuckled and strolled out of the kitchen.

_‘Shit Mama Winchester wants us together. I just wanna fuck him, not start a family. Okay maybe the family part later. Crap, he’s talking.’_

“I’m sorry I totally spaced out thinking about dinner. What did you say?”

“I asked where Tommy was.”

Your mouth dropped open in an O and you pointed down the hallway. “In his room as usual.”

“I thought so. Do you mind if I go say hi?”

“No, go right ahead. You don’t have to ask me Sam. You are like family now, help yourself. I’m gonna go get the food started.” You walked past Sam to go to the kitchen, your shoulder bumping into his muscular arm. _‘Fuck he’s firm’_

“Did you say something?”

You whipped your head around in surprise. “What? No, I didn’t say anything.”

Sam smirked and tilted his head, his eyes focusing on your cheeks that reddened as you realized you’d spoken out loud. “Oh I thought you did. I’ll be back.”

You hung your head as soon as Sam left the room. _‘I am a huge idiot.’_

Sam returned with Tommy on his shoulders a few minutes later, your son proclaiming he was going to go swimming, and you just smiled and kept chopping onions for your burgers. A huge splash a few moments later was all you heard as you watched out the patio door as Sam tossed Tommy into the pool before reaching for his shirt and tugging it off.

The sun bounced off the tanned skin of his back, muscles you didn’t even know existed rippling as he tossed his shirt to the ground, and kicked off his shoes.

“Well fuck me,” you muttered to yourself, heat pooling between your legs as he dove in a swimmers dive into your pool. You swallowed thickly as he emerged to grab your son, tossing him in the air, and letting him go a few feet away.

You shook your head and focused on the task at hand. _‘We can ogle the manny later. Must cook.’_ You looked up briefly to see Sam climbing out of the pool, his trunks sticking to the curve of his ass as he walked over to the small stack of pool toys you had pool side.

_‘Lord, please let me get through the day without sexually harassing my son’s nanny. My son’s very hot, very tall, very ripped nanny. God, I gotta get laid.’_

Awhile later you went outside to start the grill, bringing the hamburgers and hot dogs out to get them cooking. Tommy and Sam were racing each other across the water, Sam clearly holding back so Tommy could win every lap. Your heart squeezed in your chest watching the two of them together. Your ex hadn’t been the best dad, rarely being home, and when he was he often would ignore Tommy in favor of whatever was happening on his laptop at that moment. Sam was proving to be more of a dad than Tommy’s actual father.

“Guys, foods ready!”You yelled, placing the last hot dog from the grill onto a plate and stacking it on the table on your patio with everything else.

Water dripped onto the wood as you looked up to see Sam standing just a couple feet from you. Droplets ran down his chest into the matted down hair, glistening with the water that clung to it. A stray drop running down the ends of his hair fell over his broad shoulder, along his chest and down his abs before disappearing below the line of his trunks.

_‘Jesus, he looks even hotter wet. I’d love to lick the water right off his body, find out where that one went down in his shorts.’_

“So we’re eating out here?”

“Oh yeah. I don’t need you boys getting water all over my house. Sit down and help yourself. I’m gonna go grab a beer. You want one?” You tried to focus as you made a plate for Tommy, knowing if you let him do it himself he’d drown his dog in ketchup.

“A beer would be great. Thanks Y/N, and thanks for having me here. It’s been fun so far.” Dimples large enough for you to fall into, popped up on Sam’s cheeks and you blushed at his words.

“Well the funs just getting started. Wait till later when it gets dark. That’s when the real fun starts,” you giggled and gave Sam a wink before going back inside to get drinks.

_‘Oh god did I really just say that? ‘Wait till it gets dark, that’s when the real fun starts’. Fucking hell, sparklers and fireworks are not that much fun. Ugh and I winked. Stamp desperate loser mom on my forehead right now.’_

You hung your head in the fridge as you grabbed two beers and a bottle of apple juice for Tommy, the cold air cooling your flaming cheeks as you recovered from your embarrassment.

Thankfully Sam didn’t mention anything while the three of you ate, instead he let Tommy carry conversation about the games they had been playing in the pool, and how Sam had been teaching him how to properly swim without holding his nose underwater.

By the time you had finished eating the boys were dry enough to go inside, and Sam helped you take in everything while Tommy ran to the living room and put on the Spongebob marathon. Your eyes finding reasons to skip over and look at Sam as he reached to grab a bowl of potato salad off the table, or to watch him bend over to stuff said bowl onto the bottom shelf of your fridge, his ass curving towards you, making you use every bit of willpower you had to not grab it.

When he turned back around you spun to face your sink, quicking putting yourself to work on rinsing the dishes for the dishwasher.

“Did you want any help with that?” A puff of hot air hit the back of your neck, a shiver running down your spine let you know just how close Sam was standing to you. A rush of heat pooled between your thighs again as he brushed himself against you to stand off to your side.

“No-no I’m ok. Thank you Sam, you’ve been a great help.” You looked up at him, his usually bright hazel eyes darker as his tongue flicked out to wet his overly pink lips.

His gaze locked on the curve of your breasts exposed by your tank top. “Anything you need Y/N.” He reached his large hand to cup your shoulder, the rough pads of his fingertips trailing down your arm as he spoke. “Anything you need at all and I’ll be happy to help.” He squeezed your elbow and gave a sly smile before walking away to join your son in the other room.

_‘Holy fuck. Do you think he would notice if I ran to my room for 10 minutes? Make myself cum a few times with Big Blue so I’m not such a turned on mess anymore?’_ You stuffed a few more dishes in the dishwasher before closing it and turning it on. _‘Fuck. Does he know what he just did? Of course he does. Fuck, how long until Tommy goes to bed?’_ You looked over at the clock seeing it was just barely after 7. _‘Too long, damn it.’_

Keeping your cool you joined the boys in the living room, Sam getting up and grabbing both of you another beer as you tried to get into the show Tommy was watching. Sam returned with the open bottles, his fingers brushing yours as he handed one to you making you bite at your lip as he sat down next to you; the heat coming off of his body in waves made you glad he was still shirtless.

Time seemed to move at a snail’s pace, but finally the sun had gone down and you moved out to the backyard. One of the nice things about your new home was that it was near a baseball park, and you had been sent a flyer in the mail about their annual firework show. From the deck of your pool you had a clear view as they went off overhead, Tommy oh-ing and ah-ing at every burst of color that shown above him, and when you let him light a few sparklers, he was overjoyed to see them sizzle and sparkle in his hand.

Before too long you were shuffling him inside, telling Sam to do as he pleased while you got your son ready for bed. A quick bath and a warm set of jammies later, Tommy was out like a light, the full day of swimming wearing him out.

You walked out into your living room expecting to see Sam getting ready to leave, but instead found it empty. The lights around the pool reflecting off the broken water caught your eye as you watched him do smooth and even laps across it’s surface.

For a brief moment you thought of joining him, of letting the cool water wash away all the overheated feelings you’d been having all day. Instead you went over to the fridge and grabbed the last two beers strolling outside and sitting along the edge of the water. Your bare legs broke the surface as you dipped them in and waited for Sam to make his way back over to your side.

He swam over to you as soon as he saw you, and smiled when you offered him the last beer.

“Thanks.”

You shook your head. “No problem. I figured if you were making laps like that you would need something to drink, and Tommy is out for the night so no need to worry about him catching us drinking in the pool.”

Sam laughed and brought the cool bottle to his lips, wrapping them around the top. You watched as he swallowed, his Adam’s apple bobbing with every gulp, making droplets of water run down his neck.

He set his half drank bottle off to the side and you took a small sip before putting your own next to his leaned back on your hands, legs moving slowly in the water.

“Thanks for having me over tonight. It was nice to be able to spend time together. We haven’t had much of that since I started working.” Sam floated a little closer, his wet forearm touching the outside of your thigh.

“We’ve had a few dinners together, but yeah it was nice having you here. It’s been nice just seeing a man spending time with Tommy, and around the house.”

The look Sam gave you made heat fill your belly, his eyes raking over your skin as he took in your words.

“Like I said earlier, anything you need just let me know.”

Your breath hitched as Sam floated a bit closer to stand between your open knees, his hands moving to rest on your thighs, the tips of his fingers just grazing the hem of your jean shorts.

“You know, I heard you earlier.” His eyes locked with yours and he rose up slightly until his mouth was level with your ear. “My arm’s not the only part of me that’s firm.” His lips grazed the shell of your ear, and your breath quicked as you tilted your head to give Sam access to your throat. Water dripped off of him and onto your clothing as his lips skimmed over your pulse point.

He kissed over to your lips, and when they met for the first time you swore you could see fireworks again, your toes curling in the water as Sam’s hands rubbed up to your hips to pull you closer to the edge of the pool. His thumbs rubbed circles under the hem of your shirt as he pulled away, his pinkies just dipping into your shorts on your sides to hint at where he wanted to go with this.

You bit your lip and leaned back a little more to rest on your elbows as Sam pushed the end of your shirt up just enough to pepper kisses along your stomach. A small part of you remembered the stretch marks you still had there, but you let that go as his hands ran over your legs to rub over your denim covered core.

“Is this okay?” The rasp of Sam’s voice thick with arousal caught you off guard and you nodded frantically for him to continue.

Sam flicked open the button to your shorts and you planted your feet against the smooth wall of the inside of your pool to lift your hips enough so Sam could remove them. His mouth pressed warm, wet kisses to your panties as he tossed your shorts off to the side.

Harsh pants of anticipation overwhelmed you as Sam sucked a hickey into your right thigh, the fingers of his left hand pulling your panties to the side.

The moment his mouth touched you was like being hit with a thousand volts of pleasure, his tongue pushing through your folds to lick at your clit. A growl of need reverberated from his chest as Sam sucked greedily at your sensitive nub, the middle finger on his right hand just teasing at your entrance before sinking into you with ease with how wet you had been all day long.

He pumped a second digit into your pussy and licked mesmerizing circles around your clit until you were flat on your back against the cool pool deck. Your hands reached to tangle in the mass of wet hair on the back of Sam’s head as he brought you closer and closer to your release. He crooked his fingers just so, dragging them over your sweet spot, and with a harsh suck of his lips on your clit you were cumming, your walls spasming around Sam’s fingers, and he licked you through it until you finally relaxed.

Sam climbed out of the pool as you tried to catch your breath on the pavement, water dripping off of him as he reached for the tie to his trunks, the front of them tenting with his erection.

“Whoa, Sam. Wait, not out here. Neighbors could see us.” You sat up and snagged your shorts off the deck before grabbing Sam’s hand to pull him inside. “Besides my bed is much better than a lawn chair. Holds up better under strenuous activities.”

Sam chuckled and followed you inside. The moment your bedroom door was closed behind him, his mouth and hands were on you again stripping you of your shirt, bra and panties while you untied his swim trunks.

It had been so long since you’d had a man in your bed, and to have him kissing and touching every part of your body as the two of you fell into bed together, you were grinding against his length in need. You had seen how long and thick he was, the brief thought that he put Big Blue to shame with a dick that massive crossed your mind as you wrapped your fist around him and stroked him several times.

He kissed over your chest and pulled a pert nipple into his mouth, sucking hungrily at it before letting it pop free and leaning back on his heels.

“You have condoms right? I didn’t think to bring any.”

You smiled and pointed to your bedside drawer. Sam reaching over you to pull it open, his eyebrow crooking at the sight of your big blue vibrator next to a bottle of lube and condoms.

“Well at least I know I’m not going to hurt you. That thing is pretty large.”

You blushed and squeezed your hand around Sam’s cock again. “Not as large as you are, and can you please just grab one so we can do this. It’s been a long time since I’ve had a real man fuck me and Sam, I need you to fuck me.”

“Yes ma’am.” Sam grabbed the first condom he could get his fingers on and tore into it before rolling it down his length. As he finished rolling it down he reached over again to put a bit of lube in his hand to run up and down his cock before spreading the remaining bit over your folds and inside your pussy. “Don’t wanna hurt you.”

You licked your bottom lip and nodded, “Good idea. With a cock your size you’re likely to split me in half.”

Sam gave you a cheeky wink and nudged the head of his cock against your opening. A deep throaty moan escaped you as he sank in slowly, his thick length stretching you open in ways you could never imagine.

_‘Holy shit he’s huge. But he feels so fucking good. It’s been way too long.’_

He stopped when he was fully sheathed in your heat and he waited for you to adjust. You rolled your hips and his hands moved to grab your waist and pull you down hard against him.

Sam snapped his hips against you in a quick and brutal pace, the thumb of his right hand shifting to apply firm pressure to your swollen clit as he pounded your pussy with his thick cock. The rocking of his hips making his thumb move, sharp jolts of pleasure rocketed through you as he hammered his hips into yours.

Sweat and remaining pool water ran down his chest, your hands reaching to grab Sam and pull him down to your level to take possession of his gorgeous lips. The taste of beer still on his tongue as he searched the recesses of your mouth, and you clawed into his solid back as your orgasm took hold. Your walls clenching around him but not slowing down his movements.

“Fuck Sam, you keep moving like that and I’m gonna cum again.”

He buried his face in the crook of your neck, his lips and teeth marking your skin as he pushed into you over and over again.

“Promise?” He groaned his rhythm faltering for a moment, the head of his cock slamming into your g-spot and making a burst of white cloud your vision.

“Fuck, Sam!” You cried out, a third and incredibly intense orgasm washing over you, your fingers digging into Sam’s slick back, your toes curling and pushing into the backs of his thighs as your pussy convulsed around his cock.

Sam’s teeth dragged against your shoulder as you milked his own climax from him, filling the condom that sheathed him. A string of curses soaking into your flesh as he fucked the last of both of your releases out.

He panted above you and slowly pulled out, removing the used rubber, and tying it off before tossing it into the bin near your bed. Sam collapsed next to you and his massive arms pulled you into him. The damp hair on his chest tickling your face and making you sputter at the feel of the wetness on your cheek as you adjusted to lay on his shoulder.

“Holy crap I missed sex.”

Sam laughed, “Yeah, I think I’ve missed sex with hot moms.”

“I thought you said you didn’t get fired for screwing the moms?”

“I didn’t. I just got a thing for hot single milfs who like to parade around in jean shorts and tank tops.” He huffed and lifted his hand to cup the side of your face, raising your chin till he could press a sweet kiss to your lips. “I hope this doesn’t mean I’m gonna lose my job though does it?”

_‘Lose your job? Pfft with a dick like that you get a raise!’_

“Fire you? No, not for something as amazing as that. In fact as long as you keep doing what you did tonight, you just might get a raise.”

Sam moved onto his side, his eyebrow quirking at you before he moved his face within inches of your own. “What kind of raise? Does it come with better benefits?”

You leaned up to brush your lips over his. “It comes with tons of great benefits.” You crashed your mouth on Sam’s and threw your leg over his hip, feeling his cock start to swell again under the heat of your throbbing pussy as you ground into him to start another round.


	2. Pretty Girl

**Summary for the Chapter:**

> After finishing the last final of the semester, the reader gets a surprise from Sam that leaves her sated and worry free.

“I did it. I’m done! I can go die now.” You trudged down the stairs of the bunkers War Room, your boyfriend Sam standing at the bottom waiting for you.

He wrapped his arms around you in greeting, pulling you into his massive warm chest. “That’s my pretty girl. I’m proud of you and I know you passed so no more worrying about school.” He leaned down to brush his soft lips over yours, so warm and inviting.

“I’m so wiped out Sam. I just wanna sleep until next month.”

Sam pulled away, his arm wrapping around your shoulders and walking you into the library. “I know you are tired, which is why I want you to just come with me to our room. I have a surprise for you.”

You smiled up at Sam. He knew how much you loved surprises and if it was anything like the last one, you knew it was going to be something you loved.

He stopped the two of you in front of your shared bedroom door, slowly turning the knob and pushing open the door. Inside the room was dim, just a single lamp on near the door, and bathing the room in shadows. Sam had changed the usually plain white sheets on the bed to deep crimson ones and had laid out fluffy pillows along the head of the bed. There was a bottle of massage oil on the bedside table and when you looked at Sam he was smiling.

“I thought my pretty girl earned a nice relaxing massage for all her hard work. Help get rid of all that tension in your body.”

You turned to face your boyfriend, grabbing him by the collar of his plaid shirt to pull him down into a sensuous kiss, your tongue invading his mouth to lick the mint flavor from his teeth. You pulled away from his mouth to pull your shirt over your head and strip out of your clothes till you were completely bared to him.

Looking back over your shoulder, you strolled over to the bed, hips swaying as you moved knowing Sam was enjoying the small display, and crawled onto the soft fresh cotton sheets. You made a show of crawling towards the middle of the bed on your hands and knees before lowering your body down flat on your stomach in the center of the bed.

Sam reached behind his neck to tug his shirt over his head and dropped it into your pile of clothes before kicking off his shoes and removing his jeans. He walked around the side of the bed, his fingers trailing up the arch of your right foot, along your calf, and thigh. He barely grazed his fingertips over the curve of your backside and followed the slope of your spine to your shoulder.

You let out a sigh into the pillow your head lay on and you peaked over at Sam as he grabbed for the bottle of scented oil.

He knelt on the bed, throwing a leg over your thighs to straddle you, and leaning his weight back on his heels.

“This okay?”

“Mmm-hmm,” you hummed.

“Good, just relax and let me know if it’s too much.”

You let your eyes flutter closed as the snap of a cap opening sounded through the room.

Sam poured a generous amount of the lavender scented oil into his hands and rubbed them together to warm it before bringing them down to run over the expanse of your back. His long fingers and large palms slid over your sore muscles as he worked along your back and shoulders.

He kneaded his thumbs into the base of your neck, feeling the tension release, and a moan fell from your lips.

“Feel good?”

“Mmm, yes.”

Sam drug his fingers down your back, rubbing firm circles along your spine till he reached your lower back, and gripped at your sides as his thumbs made rotations over the stiff muscle in the small of your back.

“Oh Sam, right there,” an obscenely loud mewl sounded from you and you felt Sam shift down your legs, a noticeable bulge forming in the front of his boxer briefs.

The knot in your back released much to your relief and Sam moved his palms lower, his hands grabbing the globes of your ass, more sounds of pleasure spurring him on til you felt him lift and spread your cheeks apart.

Stands of Sam’s hair tickled your thighs as you felt him lean down level with you bared sex, his breath hitting your damp folds as he moved it close to flutter his tongue along your slit.

“Sam,” you breathed, a dull ache starting between your thighs.

“Get on your knees for me pretty girl.”

The hot puff of Sam’s breath along the backs of your thighs had you springing up quickly to rest on your knees and forearms.

“That’s a good girl. So gorgeous like this.” Sam ran his hands along your legs, his lips grazing over the backs of your thighs, and he pulled your hips back against his face. His mouth pressing kisses along your folds before thrusting his tongue between them to search out your clit.

He lapped over the swollen nub, feeling you resist rocking back against his tongue as he flicked the wet muscle in rapid circles, feeling you tense as you moaned. Sam sucked your clit between his lips, laving it with firm strokes before he ran his tongue up to your entrance, the tip licking and fucking into you for several pushes before going back to you clit.

A fire built in your belly and you gripped at the pillows near your head to keep yourself grounded as Sam licked and sucked at your bundle of nerves. A need to rock back in time with Sam’s mouth had you spiraling fast towards the edge, the fire inside you bursting out as you came with a cry and bit into the pillow under you.

Sam peppered kisses over your pussy, thighs, hips, and lower back; his lips dragging higher over your slick skin till his mouth was level with your ear.

“Turn over for me pretty girl. I’m not done with you yet.”

A shiver ran down your spine and you flipped over slowly onto your back, Sam balanced on his arms above you, his eyes dark with want as they flicked down to look at your nude body underneath him.

He nudged your legs apart with his knee and settled between your spread thighs as he lowered himself down to you. His cock, thick and hard, straining against the fabric of his boxers as he claimed your mouth in a kiss that took your breath away.

You rolled your hips up against Sam, his covered cock rutting into you in return as he sucked on your tongue before moving to nip along your jaw to your neck.

Sam sucked at your pulse point, his right hand trailing along your side to your breast to cradle it in his large palm, his calloused fingertips rolling over your nipple, pinching and tugging on it, turning it into a stiffened peak.

You moaned at every movement as Sam toy with your breast and kissed along your collarbone to your chest, his wet, pink lips wrapping around the neglected nipple of your right breast and sucking. Waves of pleasure rocked through you as Sam tugged on your nipple with his teeth, his right hand running down your body, and between your thighs.

He sank two fingers between your slick folds, your body jerking as he circled your clit and brought them down to dip inside you, crooking them to rub at your g-spot. His mouth moving to lap at your other breast as his fingers slowly rubbed your walls.  
You could feel another orgasm build inside you, a tugging at your core pulling tighter with every stroke of Sam’s fingers and flick of his tongue across your breasts. Like a snapping band, you felt yourself let go, a gush of slick covering Sam’s digits as he worried your nipple between his teeth.

When your walls stopped spasming around his fingers, Sam pulled them free, bringing them up to his mouth to suck your juices from them.

Watching his eyes close in pleasure at your flavor and give a hum of delight made you ache for more.

“Sam, please. I need you.”

He brought his lips to yours, letting you taste yourself on his tongue as it brushed over yours.

“In time pretty girl. Right now is about you. You’re so good and you look so beautiful like this. Are you okay to let me taste you again?”

You licked your lips and nodded, watching a Sam’s dimples appear as he smiled and crawled down your body till he could settle on his stomach between your open legs.

He pulled your thighs over his broad shoulders, his lips and hair tickling the insides of your legs as he scattered kisses over them, and licking the bit of your arousal that covered your flesh.

“You’re so beautiful and you taste amazing. I love seeing you like this. Having you spread out before me, waiting. So good for me.” The low husk of Sam’s voice sent desire coursing through you and Sam moved his mouth closer to breathe in your scent.

“God, you smell good too,” hot puffs of air across your damp folds made you whimper in need and Sam surged forward to press his tongue flat over your slit.

He lapped at your cunt, his tongue pushing through to rub at your clit, swirling it in quick motions, and making you cry out in need. A finger slowly entered you as Sam continued to flick at your swollen nub, a second following soon after as you cried out for more.

Overwhelmed with pleasure from Sam’s skillful mouth and deft fingers had you moaning wantonly, letting your desire and need push you to be as loud and obscene as you wanted to be.

“That’s my pretty girl. Gonna cum one more time for me? One more time for me before I give you what you really want.”

You mewled a yes and Sam dove back down to ravish your pussy, his fingers now joined by a third stretching you open enough to accommodate his impressive size.

The combined effort of Sam’s lips, tongue, and fingers had you careening over the edge. His name a shout that left your throat feeling raw as wave after wave of pleasure rocked through you.

Sam scattered kisses over your body as he moved back up to face you, settling to lay beside you, propped up on his elbow as you panted to calm your quickly beating heart.

“How you doing pretty girl? You alright?”

You swallowed thickly, your mouth dry, and you tried to lick your lips to bring them some moisture.

“Yeah,” you panted. “I’m good.” You turned your head to look at Sam, never having noticed he had taken his underwear off until you looked down to see him leisurely stroking his full length.

“That’s my pretty girl. Think you can handle one more or did you want to stop?”

You rolled to your side lips crashing against Sam’s, your fingers tangling in his hair as you slide your thigh over Sam’s hip, his hand trapped between your bodies. Sam moved his cock to your entrance, slipping inside you with a groan.

He removed his hand, grabbing a firm hold of your thigh and thrust inside you completely, using the momentum he had to roll you onto your back without breaking your connection, and rocking his hips into yours. Slow drags of his cock along your overstimulated walls had you crying in pleasure, his mouth attacking your neck and chest as he pawed roughly at your hip and thigh still wrapped around him.

“Sam, harder, faster,” you panted and you felt him grin against your breast.

“Not yet pretty girl. Gonna make this one you never forget.”

You groaned in frustration, feeling the deep, long thrusts building a dam of pleasure inside your belly that you wanted to burst already. Rocking your hips against Sam’s frantically was no use as he pinned your hip to the mattress, firm deep strokes driving you higher but no faster than before.

“Sam, please. I need it, need more. Please,” you begged.

“Soon pretty girl, just enjoy this. You feel so good, so wet and tight around my cock. Could spend forever inside you.” Sam’s lips wrapped around a hardened bud and sucked, sparks shooting down your spine straight to your clit, and making you tense, squeezing your walls around Sam’s shaft.

Sam gave a low grunt and pulled away from your chest, his arms moving to cage you in on both sides, and you wrapped both your legs around his thighs just before he started pounding into you. Fucking you straight into the rumpled, red sheets, and making you cry out at the much needed stimulation. The bone of Sam’s pelvis grinding against your clit with every hammered push of his hips and the dam that had been building in your belly broke.

Flashes of white clouded your vision as you closed your eyes in ecstasy, Sam giving a shout of his own as he pumped steady streams of his cum, wet and warm, deep inside your pulsating walls. His thrusts slowing until he felt you relax underneath him and he stilled himself to pepper kisses along your neck and lips before slowly removing himself from you to lay beside you, and catch his breath.

You snaked your hand along the sheet to find Sam’s, intertwining your fingers as you laid shoulder to shoulder.

He lifted your hands and pressed a kiss to your knuckles.

“You okay?” He mumbled into your skin.

“Mmm-hmm, I’m good. Very good. I needed that.”

“Done worrying about school?”

You shook your head. “Not anymore even though I know I failed my final. I don’t really care right now.”

Sam released his hold on your hand to wrap his arm around your shoulders and pull you in snugly to his side.

“Good, I’m glad. Get some rest baby. You’re gonna need it for round two.”

You looked up at Sam quickly. “Round two? I don’t think I can even move right now.”

Sam laughed, “that’s why I said to rest. You’ll need the energy for what I want to do next.”

You let out a sigh in anticipation and curled up next to Sam, letting your mind wander to what might be next, and drifting to sleep safe in his embrace.


	3. Once is Never Enough

**Summary for the Chapter:**

> Being a plus size woman doesn’t stop you from hooking up with Dean Winchester in the back room at Harvelle’s Roadhouse and he’s more than turned on by your confidence and thick curves.

Dean figured Sam catching the flu wasn’t the worst thing in the world as he watched your ass sway back and forth in the tight jeans you were wearing. The denim hugging the curves of your ass and hips perfectly, giving Dean the kind of show he’d never be privy to had he not been forced to stay at the roadhouse with Ellen.

Jo was thankfully away, back at college where she belonged and Dean no longer had to pretend that your curvaceous body wasn’t exactly the type he wanted to lose himself in. Dean had fantasized about you more times than he could count and watching you scrub at a table top everything jiggling in time to your movements had Dean’s cock hard and pressing against his zipper.

He kept his eyes on you all day, his green eyed gaze straying down the front of your top to your ample breasts, wishing he could bury himself in your cleavage. He’d give anything to lube up his dick and let it get consumed in between the fleshy mounds.

Two days in a row Dean would sit at the bar and watch you work, getting lost in fantasies that would leave him so hard he could only make it to the restrooms single stall before he had to pull out his cock for a quick release. He’d cum more times in his fist in that bathroom than he did inside random bar flies in the last month and it was all because of how much he wanted you.

Despite you pants size you never thought of yourself as any less attractive than your thinner counterparts. Your size 22 ass was just as hot in a pair of cut off jeans as your size 6 best friend’s. Everyday you got looks at work from men who were patrons and every night you went home with plenty of tips. Life was good at Harvelle’s Roadhouse and they got even better when Dean WInchester showed up.

Dean was the kind of guy you had originally pegged as not into fat chicks but after only 30 minutes of working the floor, dropping off drinks, and clearing tables you noticed Dean was very into you. His gorgeous evergreen eyes following you everywhere, looking like he was ready to pounce on you at any moment and you knew you could have some fun with this one.

You purposely wore your tightest jean even though the button made an indent in your belly that you knew would be aching at the end of the day, swinging your hips while you worked, putting a little extra sway in them as you stolled by him, and scrubbed harder than necessary to make sure your ass was wiggling in Dean’s direction. You even went as far as to take your bra off near the end of your shift, your nipples stiffening behind the bar as you reloaded the beer cooler; Dean’s eyes laser focused on them poking against your shirt.

“Hey Winchester, think you could help me close up for the night?”

“Sure thing, sweetheart.” He licked his pump lower lip and you tossed the keys to the front door to him, his one handed catch sending heat to the apex of your thighs.

“Get Larry out of here and lock up would you? I’ll meet you in the back and you can help me get the kegs moved out back for tomorrow mornings pick up.”

“Be right back, sweetheart,” he replied with a wink.

You disappeared into the cramped back storage room, leaving the door open for Dean as you flicked on the single light overhead.

Dean Winchester was sex on bowed legs and you were determined to tease him until he couldn’t take it anymore and took you. You’d heard enough stories to know he knew what he was doing and you were no blushing virgin either. The moment Dean walked through the backroom door, you were on him, your lips smashing against his, tongue pushing into his mouth, hands gripping at the leather of his jacket while his tangled in your hair.

The fight for dominance became like a dance as you backed Dean up against a bank of shelves, pushing his jacket off his shoulders and tugging at the henley he wore, your fingers desperate to feel the hot, taut skin underneath.

Dean pulled his shirt over his head, knocking a bottle of wood polish off the shelf in his dash to rid himself of his clothing, his hands immediately grabbing at your top, ignoring the fallen item. A husked, ‘fuck’ fell from his parted pink lips as he saw your bare breasts hanging free as he tossed your shirt to the now growing pile on the floor near the door.

“Damn Sweetheart, your teasing tonights gonna be the death of me.”

You stepped back into his embrace mouthing over the side of his jaw and catching the soft lobe of his ear between your teeth. “I hope so sugar.” You licked the shell and latched onto the side of Dean’s neck, sucking sharply, nipping at the bruising flesh before running your tongue soothingly over the mark you’d made.

Dean gripped your waist tightly, pulling you closer, and grinding the denim rough bulge in the front of his jeans against your soft belly, your breasts smashed against the firm expanse of his chest, your nipples hard, sensitive and straining for attention, more heat traveling straight down to your throbbing sex.

You clawed down Dean’s arms, the muscles rolling as he gripped you tighter, your mouth reclaiming his as you reach down for his belt, deft fingers releasing it before popping the button at the top of his pants.

His hands suddenly reached for your wrists, stopping your hands just as you started tugging at his zipper. “Had enough of your teasing darlin’,” he drawled. His body moving forward, pushing you back a couple steps until you collided with stacks of beer boxes. Dean groping at your jeans, ripping them open with a few flicks of the wrist. “It’s my turn to tease and sweetheart, I don’t tease lightly.”

Dean tore the remainder of your clothing down your legs, your jeans and panties getting tangled around one of your sneakers as he dropped his lucious mouth to your left breast, tongue, lips, and teeth pulling out pleasure you hadn’t known you could feel till that moment. swirling, flicking, and tugging the taut bud, moving to the other side just as a calloused hand moved down your belly, skirting over the striped, plush flesh to find your folds dripping as he probed two fingers between them. Sinking them down to rub the overabundance of arousal coating your opening up to your clit, moans bursting out of you as he firmly stroked in tight circles.

He pulled away from your chest with an obscenely wet pop and before you could say anything Dean was dropping to his knees, his fingers trailing down to thrust up into your cunt before slipping back out and scissoring open your labia, the flat of Dean’s tongue licking over it as you spread your legs further and leaned back against the beer boxes, hums of delight drifting up from where Dean teased between your legs.

“Fuck, Dean. That feels so good. Don’t stop baby.” You panted and tangled your fingers in Dean’s shot spikes, tugging him where you wanted him and moaning loudly for more. The digits holding you open moved down and you cried out as he slammed them into your sodden hole, his lush lips wrapping around your swollen clit to suck while he rubbed that sweet spot inside you in rapid even strokes.

“Yes, oh God. I’m gonna cum. Fuck, yes, Dean! I’m gonna…” your walls pulsed and Dean stopped to pull away completely.

“Payback for all the teasing sweetheart. Turn around, let me see that ass you’ve been wiggling at me all night.”

You hopped off the box you were leaning on and turned around, bracing one hand on the stack and the other against the wall in front of you. The sound of a belt hitting the floor was quickly followed by the sound of Dean spitting something out of his mouth. A quick look back over your shoulder revealed it was a condom wrapped and Dean was in the process of rolling it down his dick, one you’d not seen till now. Thick and hard, the tip an almost angry shade of red as he inched closer and smirked at you.

“Like what you see darlin’?”

You laughed lightly, “yeah but I’d like it a lot better if it was fucking my pussy.”

Dean brought a hand down swiftly across your ass. “Oh believe me baby, this pussy is about to be full.” The fat head of Dean’s cock pushed through your soaked folds,nudging the tip against your clit a few times, rocking back and forth, coating his cock in your juices before he sank his thick length into your tight, wet heat all the way to the hilt.

“Fucking tight sweetheart. Never had a dick this big before?”

You mewled in return and pushed back, the delicious stretch of your cunt a welcoming feeling as you fucked yourself back against him. The clapping sound of his pelvis hitting off your ass was almost comical as he thrust with abandon and your breasts hung, swinging heavy in front of you with every push.

Dean pounded away at you, his fingers digging into your meaty hips, slamming you back against him, your pussy gripping and sliding over his cock perfectly. “Shit you feel good. Could fuck your pussy all night.” he growled, his hand skimming over your hip and up your back to grab your shoulder.

You reached quickly for the shelf next to you as Dean used the grip he had on your shoulder to pull you back harder onto his throbbing cock, fucking himself into you hard and fast, as extra beer glass falling off the shelf followed by another and another as the momentum of his thrusts were causing you to tug the shelf in a pitiful attempt at stability.

Neither of you paid it any mind as you felt the heated pull between your legs, the hand Dean still had on your hip coming around to toy with your clit in time with his hips, his lips peppering kisses over your sweat covered back.

“Done teasing sweetheart?”

“Yes,” you sobbed, your body so overwhelmed with pleasure and on the very edge of a intense orgasm.

“Good, be a good girl and cum on my fat cock.”

Dean’s words, the push and pull, the swift circles all overcoming you in a blindingly intense flash, moans loud and bouncing off the walls as your pussy pulsed around Dean’s stiff length.

He kept pushing, his movements only slowing till your walls stopped clenching. His sudden withdrawal from you surprised as were his order.

“Turn around and get on your knees.”

You moved without question and by the time you had yourself level with Dean’s cock it was bare, condom tossed haphazardly aside as he gripped the base.

“Open. Suck.” You followed the command, the dull remaining taste of lubricated latex and the salty tang of precum on your tongue sent you into overdrive as you swallowed him down. Fast bobs of your head, hallowed cheeks, tongue gliding along the vein and over the head as you pushed to take as much of his cock as you could into the heat of your mouth. Long fingers tangled in your hair, a firm hand guiding your head as your hands gripped strong, muscled thighs.

“Just like that. There you go. There’s a good girl. Swallow for me baby. Enjoy it,” he growled as he filled your mouth with his load, some dripping out around the head and falling onto your breast to run down to your belly.

You licked him clean and leaned back to wipe the drops off your stomach and tits.

Dean groaned loudly above you and bit at his reddened bottom lip. “I thought I just taught you not to tease?”

You stood up, wrapped your arms around Dean’s neck as his hands settled to grab the globes of your bare ass.

“I guess you’re gonna have to teach me again. Once is never enough for me baby.” You nipped playfully at Dean’s lips as he spanked you again.

“Once ain’t enough for me either darlin’.”


	4. The Coat Check Room

**Summary for the Chapter:**

> Your ex Dean agrees to be your plus one at a wedding you’re attending as a bridesmaid, after a few drinks things get a little hot and heavy in the coat check room while you’re looking for your coat.

Weddings weren’t Dean’s usual thing, in fact until you called begging him to go with you as your plus one, he’d never been to any. You were his best friend, once upon a time hunting partner, and ex whatever it was the two of you had going a few years back. He’d grabbed his Fed suit and made the drive out to you, your smile and open arms a bonus after such a long drive when he arrived.

It hadn’t been as bad as Dean thought it was going to be. The ceremony wasn’t overly long and the red bridesmaids dress you wore showed off all the curves of your body that Dean loved. He’d enjoyed the food at the reception, and although the music wasn’t quite his taste it still wasn’t too bad.

The reception was in full swing and the both of you had enjoyed the open bar a bit more than you probably should have as your hand stroked over the muscle of Dean’s thigh, moving higher until your hand brushed over his length; his own hand slipping under the table to move your hand till it covered him completely.

Dean squeezed your hand, his cock twitching, and growing under your palm as he leaned his mouth closer to your ear.

“Why don’t we get your coat and get out of here? Have some fun like old times.”

His breath swept hot across your neck and you gave him one more squeeze before letting go and standing from your chair.

“I thought you’d never ask.”

With a sly smirk on his face, Dean rose and strolled out of the ballroom with his large hand pressed to the center of your back, his thumb caressing the silky fabric against your skin as he rubbed it in short rotations.

The coat check room wasn’t too far but to your surprise it was unoccupied, the top half of the door still open revealing a room full of jackets but no attendant.

You let out a sigh and turned to face Dean. “Now what do we do? I’m not leaving without my jacket. It snowed this morning and no way am I going out there in a sleeveless silk gown. I’d freeze my tits off.”

Dean grabbed you around the waist and pulled you flush into his chest. “Wouldn’t want that, your tits look fantastic in this dress.” He licked over his bottom lip, his lips moving towards yours, and stopping only a breath away. His free hand came up to cup your cheek, the warmth of his palm sinking into your already flushed cheeks as he whispered, “let’s just sneak in and grab it. Need to take you back to your place and be reminded of all the good times we used to have.” He brushed his mouth over yours, his plush lips leaving a tingle behind as he pulled away and reached over to the other side unlocking the door for the two of you to enter.

He held it open for you, gesturing with his left hand for you to go first and walked in behind you, closing and locking the door as he had found it.

You wound through the racks trying to find your black coat among a sea of others. Dean coming up behind you as you continued to search wrapped his arms around your middle, his lips skirting over the side of your neck.

“Found it yet?” He pressed himself against you, the whiskey on his breath making you dizzy, and his hard cock in his slacks making you push your ass back against him.

“Mmm, no. Someone is distracting me.” You let your head fall to the side, Dean’s hands moving to your hips to grope at the fabric, slowly raising it up your thighs as he mouthed along the curve of your shoulder.

Your hands fell to cover his, squeezing before running up along your sides to touch your own breasts through the silken material, your nipples becoming stiff peaks under your own touch before you wove your fingers into the hair at the nape of Dean’s neck; tilting your head to press a kiss to Dean’s lips, wet and swollen red.

He moaned into the kiss, his lips not leaving yours as he spun you in his arms. With long strides, Dean moved you back across the room until the floral, textured wallpaper scrapped along the exposed part of your back.

His tongue licked over yours, the whiskey taste on his lips mingling with the champagne on yours as you kissed him back, your hands moving down to the lapels of his jacket, and pushing it off his board shoulders. Your hands dropped to his waist, deft fingers tugging his shirt out of his pants before moving to work on his belt.

Dean slipped the sides of your dress up until it was bunched up around your waist, his greedy right hand plunging under the band of your panties to slide through your damp folds, his thick fingers circling your clit, making you moan out as he dropped his mouth to suck at your throat.

His slacks fell free around his ankles as you unsnapped them, his cock straining hard against the fabric of his boxer briefs and leaving a wet patch where the tip lay leaking. You sought him out, your hand snaking under the tight fabric to get a firm grip on Dean’s cock, a hiss at the contact had him thrusting slowly into your fist.

“Fuck, you still remember what you’re doing.” Dean groaned into your skin as your thumb rubbed over the head of his cock.

You leaned away from Dean’s mouth, your free hand pulling his from your panties as you sank slowly to the ground in front of him. Removing your hand from his length you pulled his boxer briefs down his thighs. “Yeah I do. You still taste as good as the last time I had my mouth on you?” You reached up around your neck to untie your halter before wrapping your fingers around the base of Dean’s cock and swipping the flat of your tongue over his slit, a hum of delight bubbling up your throat at the pre-cum flavor that burst over your tongue.

Wrapping your lips around the crown, you sank your mouth down taking as much of his length into your mouth as you could, letting the tip bump gently against the back of your throat before bobbing up and down his thick shaft. Your cheeks hollowing on every bob up, creating the much needed pressure around Dean’s cock with your lips.

He shifted above you and looking up at him through your lashes he was supporting himself with his left arm braced against the wall, and as your eyes met his, he threaded the fingers of his right hand into your hair knocking several of the bobby pins holding it in place to the floor.

“Fuck, your mouth feels amazing.”

You smirked around Dean’s length, your free hand unclasping your strapless bra and watching as Dean’s head fell between his shoulders, his eyes closing as he bit at his bottom lip. Slowly you licked up along the vein on the underside of Dean’s cock one last time to hear him let out another groan before letting him pop free of your lips.

Peppering kisses along Dean’s lower belly and thighs brought him back to you enough to help you up, your hands going under your dress to tug your panties off, the top of your dress dropping down and pooling around your waist.

Dean’s mouth collided with yours, his hands reaching for your thighs lifting you up off of the ground to line up your dripping pussy with his thick cock as your arms wrapped around his neck. He slowly sank you down over his length, his cock stretching you as he bottomed out.

“Fuck, your pussy feels good too,” he murmured against your lips. He pulled out slowly before slamming back in, your walls fluttering around the delicious drag of his cock through your folds.

“Jesus,” you groaned as Dean fucked you hard against the wall, his mouth dropping down to pull one of your nipples into his mouth, sucking greedily at your flesh.

Your fingers tangled in Dean’s hair, the slightly overgrown part along the top of his head letting you get a firm grip to pull his mouth away from your breast and back up to yours . fucking yourself down onto his shaft as he pistoned his hips up into you.

Dean’s crisp white shirt clung to his back with sweat as you held onto him feeling your pleasure mounting with every thrust. The drag of Dean’s pelvic bone over your swollen clit and the pulsating length of his cock frantically hammering at your cunt had you moaning out in bliss.

The sound of the coat check door being unlocked had Dean slamming his hand down over your mouth to keep you quiet. His breath fanning hot over your neck and ear as he husked, “be quiet, they’ll hear you.”

A shiver ran down your spine at the thought of getting caught and Dean’s thrusts never faltered as you tightened your legs around his waist, digging the heels of your shoes into his ass to pull him in deeper.

Dean’s eyes locked with yours and without a single word his green orbs told you to cum, to let go and milk his own release from him before the two of you were caught. Like a flash of lightening, pleasure ripped through your core, your teeth clamping down on Dean’s palm as your walls squeezed around his length. He followed with a grunt, his cock pressing in deep releasing warm and thick inside you.

The attendant moved around at the front of the room, and the sound of hangers moving had Dean lowering your legs to the floor before pulling out. He snagged your bra and panties from the floor before pulling his underwear and pants back up. He grabbed his jacket off of the floor just in time, as a petite blonde rounded the rack that had been obscuring the two of you from her sight.

“Um, you aren’t supposed to be back here.”

Dean smirked and moved in front of you, giving you time to jam your bra and panties into your small purse and make double sure the strap around your neck was tied tight enough not to flash anyone on the way out.

“Sorry about this sweetheart. You see my date and I were ready to head on out and you weren’t around. It’s too cold outside for a lady in a dress like hers to go out without a coat on. I figured it would be alright if we came in real quick to look.” Dean flashed a smile and you watched the poor girl practically melt into the floor.

“It’s okay. Did you find the jacket?”

You stepped around Dean, your bag stuffed full and the beginnings of Dean’s cum starting to leak down between your thighs.

“You know what, we didn’t. Can you help me?” You held your claim ticket out to her and she reached over your shoulder to grab your coat.

“It was right behind you. You must have missed it.”

You laughed and took the jacket from her before thanking her and slipping into it. Dean slid his jacket back on as well before wrapping his arm around your waist guiding you out of the hotel.

“You know, we are lucky she didn’t catch us.”

Dean laughed. “Oh, she caught us. Didn’t you see how red her face was? She totally saw us. Probably on the monitor she has on the little check in desk she’s got. I think she enjoyed our little show, don’t you?”

You scoffed and stopped just short of the Impala. “You knew there was a camera on us the whole time and you didn’t say anything? Pig.”

“Oh sweetheart you know you love it. Still up for a couple more rounds tonight?” He quirked his brow as he opened your door for you.

“You know I can’t say no to you.” You sighed as Dean smirked, closing your door and making his way around the car to take you back to your place for rounds two, three, and four.


	5. What's the Stakes?

**Summary for the Chapter:**

> When Dean loses a bet, the reader has a little fun with her win.

“This is weird.”

“No it isn’t. I kinda like it.”

Dean quirked his brow and gave another strong, hard thrust, your toes curling as the textured sleeve covering his cock pushed over your g-spot.

“Fuck!”

“This is seriously working for you?”

You nodded, a knot of desire building low in your belly with every drag of his cock.

“Damn.” Dean increased his movements, determined to make you cum and fulfill his end of the bet.

“Oh fuck, right there! Fuck! Dean!” A blinding orgasm washed over you, the quickest you’d ever had as your pussy convulsed around the ridged silicon toy.

“Jesus fucking Christ babe.” Dean gasped, pulling out of you slowly to tear the thick clear penis sleeve extender off his swollen red length. “I’m glad you enjoyed that because I couldn’t feel anything until you started to cum. Your pussy always grabs onto me with a death grip when you cum.”

You looked over at Dean, his length still hard and curled up against his stomach.

“I’m sorry baby but I’m still glad I won that bet.”

* * *

You put your pool cue back up on the bar wall, securing it in place before turning back around to face Dean. ”Okay so you won this time but you’ve been hustling this game since you were old enough to see over the fucking table. We need a real challenge.” You scoffed and walked back to your high top with Dean

“A real challenge huh? Like what?” He threw his arm over the back of your chair, his hooded olive eyes boring into yours.

You scanned the bar crowd, noting the men that sat shoulder to shoulder at the bar and at near by tables.

“I got it. First one to get five phone numbers wins.”

Dean looked around only counting two other women besides you. “No way. One number, ain’t enough women in here for five.”

“Three then and at least one has to be from a guy for you.”

He sighed and rolled his eyes. “So what’s the stakes? What do I get when I win?” Dean wiggled his eyebrows at you, his attempt at being seductive only making you laugh.

“Stop that, nerd. How about we go shopping? Winner picks a toy to use on the loser.”

Dean nodded and took a pull off his beer. “Oh you are so on.”

Two hours later you had managed the numbers of four different men as well as the number of your waitress, her hips swaying away from you with a little extra bounce. You watched Dean get turned down for the fourth time in a row.

He saw you sitting, a fresh beer in your hand and came over, flopping down next to you.

“I give up. I got two, the third was impossible. How’d you do?”

“Five.”

“Five?’

“Yup!” You pulled five folded napkins out of the front pocket of your jeans, dropping them on the black table top. “Boom, count ‘em. I win and take note of that one.” You pointed to the one the waitress had given you

“You got our server too. Holy shit babe. Alright you win. Let’s go get a vibrating cock ring or something.”

You laughed and grabbed your coat knowing what you wanted to get was of the ‘or something’ variety.

Together you wandered the still open sex shop, wall displays of different kinds of toys grabbing your attention. Dildos, vibrators, cock rings, and lube of every flavor, all things you walked passed until you came to the aisle you were looking for.

Multi colored and sized butt plugs, fleshlights and masturbation sleeves lined the wall until you reached the end.

Penis extender sleeves, ranging in colors and textures filled two separate shelves. A clear one with swirled ridges catching your eye right away.

“This one. This is it.” You grabbed it off the shelf and handed it to Dean.

“Seriously? I don’t think I need any help in the length department babe.”

You grinned mischievously. “It’s not for length, it’s for texture. Those ridges are gonna rub inside my pussy every time you thrust into me and you’re gonna make me cum so hard I practically pass out. A girl friend of mine used one and said it was some of the best sex she’s ever had.”

Dean examined the packaged toy. “I don’t know.”

“Come on baby. I did win and a bet is a bet. If you hate it, we can take it off.”

“Okay, but if this really sucks you owe me.”

You giggled with joy and snagged the sleeve from Dean, making your purchase and going back to your shared motel room.

* * *

You rolled onto your side to face Dean, his eyes were closed and you figured he was trying to will away the throbbing erection he was still sporting. Leaning closer to him, you pressed a kiss to his shoulder, your hand laying flat on his chest and trailing down until you could wrap your fingers around his cock.

Dean gave a soft grunt as you started stroking him, your mouth working in small kisses and nips over Dean’s chest, your teeth scraping over his nipple. His back arching as pre-cum leaked from his cock all over your fingers.

Moving onto your knees, your mouth traveled south, tongue flicking out to taste the wet tip before encasing Dean’s rock hard cock inside your warm mouth. Lips sealing around the thick girth, tongue sliding around the head and down the shaft till your nose pressed again the thatch of curls along the base. You swallowed around your gag reflex, Dean groaning out at the pleasure you were giving him, the feel of your throat constricting around him almost more than he could take.

Hallowing you cheeks you sucked up and down Dean’s length, the velvet head leaving traces of pre-cum on your tongue every time you lapped over it. The heady need to make Dean cum, to feel him tense under you, to hear him groan and growl for you as his heavy cock left thick streams of his cum in your mouth driving you to keep going.

Sucking harder, licking up and over the crown with every bob of your mouth up as you reached a hand to cradle Dean’s tight sac, your thumb stroking over the taut wrinkles as you bobbed down and buried your nose against his pelvis again.

“Fuck babe, I’m gonna, fuck!”

The raspy gravel of Dean’s words sent sparks down your spine just as he exploded over your tongue. His cum flooding your mouth as you greedily swallowed every drop only stopping and pulling away when his cock stopped twitching between your swollen lips.

“Jesus babe,” Dean gulped in mouthfuls of air as you moved back onto your side against him.

“I know you thought the sleeve was weird but you liked that didn’t you?”

Dean gazed over at you lazily, his lids hooded as he smirked. “You know that I did babe.” He leaned over pressing a deep kiss to your lips, humming at the leftover taste of his own cum on your tastebuds. “But let’s not use that **thing** ever again. If I’m gonna fuck you, I want to at least be able to feel it.”

You giggled and reach for the blanket on the end of the bed covering you both as you snuggled into him. “Yeah, we’ll see about that.”

“Wanna wager another bet?”

“You know I do. What’s the stakes?”


	6. Smooth

**Summary for the Chapter:**

> Sometimes Jared needs Gen in a whole other way and he is more than willing to be on the receiving end of her cock.

Genevieve smooths her petite hands over the deliciously creamy skin of Jared’s sharp hips, nails just grazing the flesh to tease him, dotting it with goosebumps as she tails her hands down to squeeze at the mounds of his ass cheeks, and she leans forward to kiss at the tip of his tailbone. The hot, wet point of her tongue flicks out and licks down, catching on the cleft of his ass, the whimpers falling from the overly pink lips of her husband driving her to spread the globes apart and drag her tongue down further.

Lapping at her husband’s puckered hole, swirling it in circles, working it in and out to slowly open his asshole to her as he whines. Face down, scrunched nose buried in the pillows, sweat already coats his beautiful, tanned body. She longs for him to make these sounds and she teases him to hear more, teases until he’s panting and she can stick her tongue in past the rim of tight muscle.

The flesh colored cock weighs heavy between Gen’s thighs and she can feel it swing with her motions as she eats out Jared’s ass. The thrill of getting to watch it stretch him open over it, splitting him down the middle, pulls at her gut. She wants to see him stuffed full so fucking bad, but knows she has to show restraint. First she has to get him ready, turn him on, open him up, make him pliant and warm beneath her touch before fucking him into oblivion.

Jared starts to beg and Gen is feeling generous tonight as she sits back and reaches for the bottle of lube she laid next to her on the bed before she started touching him. Flipping the cap open, she watches the clear liquid ooze out of the opening; much like Jared’s thick cock that’s been hard and drooling along the sheets since Gen tightened the first strap of her harness.

Thick droplets land on her fingers and she spreads the cool slick over his fluttering hole, watching as it clenches for her, wanting desperately to be filled with something, and with the slowness of molasses, she sinks in a single digit. Her brown eyes are mesmerized by the ease of muscle opening to her and she swiftly pulls it back out to insert a second.

He hums into his forearm, digs his elbows into the mattress and wipes the sweat off his forehead while feeling the burn of being stretched when she pushes in a third, knowing that it will take at least four of her fingers fucking his ass before he can take her cock. His dick begs for attention but he doesn’t touch it, knows better than to touch it because if he does Gen will stop and he needs her to keep going. Jared needs this more than he’s needed anything else all week.

Fucking a fourth finger into Jared’s tight ass takes more restraint on his part than hers not to speed things along. She’s leisurely with her thrusts and he tries to not push back, to not beg for more, he knows and so does she that soon he will be full of her cock and spilling his seed over their bed.

Her lips pepper over the sweaty skin of his lower back, obscene squelches of her slicked fingers gliding easily through his open hole. “Such a good boy for me, baby. You ready for my cock?”

He whimpers, raising up onto his thick, wide hands, arching his back to present himself as Gen pulls her digits loose; sweat drips from every inch of Jared’s body and his hair hangs loosely over his eyes. Looking back over his broad shoulder, he shudders at the sight of his wife stroking the fake shaft between her delicate fingers, lube making it shine in the light of their bedroom. For a brief moment, fear coils in his gut as he realizes it’s as big as he is, and they’ve never used this one before. He’s never had anything that long or that wide inside him, and a thick glob of pre-cum dribbles out of the slit of his twitching purple-headed cock because he knows he wants it anyway.

“Please,” he begs.

“Please what, baby?” She rubs the crown against his hole, her hand holding it around the middle to keep it straight as she teases him.

“Please, fuck me, Mommy.”

Her cunt throbs behind the dildo’s base at his name for her, knows she won’t be able to hold back once she sinks into him.

“There’s Mommy’s good boy. Hold still, baby, I got you.” She moves her hips, pushing just the head in, watching his puckered hole swallow it up and she grabs the lube to drizzle more down the crack of his ass, letting it slide down and wet her cock as she thrusts forward. Her nails digging into the soft flesh of his ass as she lets go of the dildo and grabs onto him.

She bottoms out, eyes staring unashamed at the display below her, the curve of her hips flush with Jared’s ass, waiting for him to adjust to the large intrusion. She loves him like she’s never loved anyone before and the last thing she wants is to hurt her baby. “So gorgeous, sweetheart.” Her hands smooth up his sides and back down before she pulls him apart again, the need to watch herself move out of him strong and unyielding.

His hole is stretched taut over the fleshy silicone member and Gen tips her hips back away so slowly that Jared’s nearly crying in desperation. It’s like torture and he wishes he could see what his wife is seeing.

“Mommy?”

“Yes baby?” Her voice sounds like silk and Jared shudders at her tone.

“Fuck me, Mommy. Please.”

“Oh, honey, begging for Mommy’s cock like a whore.” She pulls almost all the way out, the ring of his asshole just clenched around the head. “Take my cock like a good fuckin’ whore.” Something inside Gen snaps and she thrusts forward in a brutal, bruising rhythm of skin on skin, the slap of her bouncing off his pillowy ass sounding beautifully in their massive bedroom.

“Such a good boy for ME, good little whore taking all of Mommy’s cock.”

He cries out as Gen spreads her knees further apart, lifting her left to press her barefoot to the mattress and finds that perfect spot, hitting his prostate over and over and Jared just arches back, taking it like the whore he is for his Mommy.

She pounds away at him, his willing body taking every inch, and she’s hitting against him so hard the base keeps bouncing off her swollen clit. The slick from her cunt smeared over the underside and making the slide of rubber bring her towards climax just as much as it was Jared on the other end.

The need to have him come undone on just her dick fills her and she grabs Jared’s waist to help keep herself stable as she fucks him. “Gonna have you cum on my cock, baby. Wanna see that slutty little wrecked hole of yours sucking at my dick. Come on, Jared. Give Mommy what she wants.”

Jared’s stomach knots, abs flexing at Gen’s filthy words. She’s using his kinks against him, knowing that her voice paired with her pounding would send him over. His untouched cock swells thicker and pulses out rope after rope of gooey opaque cum, staining the sheets underneath his massive frame.

The excitement of watching Jared’s cock twitch beneath him and his asshole fluttering around her fake creamy colored cock flips a switch in tiny little Genevieve’s body, spurring her to pull him back, bouncing him against her. “Not done with you yet, whore. This ass is mine until I say otherwise. Fuck my cock.”

Jared’s head is still swimming from his release but his body goes by memory and fucks back onto Gen’s member, feeling it hit over and over, stretching and teasing his opening, shooting him back towards that edge again in no time. But he holds back, Gen’s making that moaning sound she makes when she’s close and he won’t cum a second time unless she cums first. They have rules and it always makes it better to know he’s made her cum just as she had him.

She rolls her hips, hard clit rubbing the base as she fucks her husband, and although this was just about making him cum for a second time on her behalf, there is no way she can keep herself from cumming this time, so she reaches around Jared’s side to grab his dick. He’s soft from cumming but she pumps him in her fist anyway, lets his cock slide limply against her palm as she ruts behind him.

“Make Mommy cum, baby.” It’s a mewl of pure need, almost like she was begging, and Jared presses his ass back, her cock pressing hard against his prostate as he grinds against her. They both gasp at the pleasure, Gen’s pussy clenching around nothing as she cums, her juices leaking and staining the straps of her harness.

Jared can’t stop this second time and with a limp cock in his wife’s hand he cums for the second time tonight. The load he spills is considerably less this time, but still it feels just as powerful as Gen refuses to stop rutting her cock against the sweet spot in his ass, milking it, and it takes Jared crying fat, wet tears and begging for her to stop before she does. Stilling her hips and pulling out real slow.

“S’okay, baby. Mommy’s got you. You were so good, baby. So good, thank you, baby.” She crawls around on the bed as Jared falls down flat on his belly, tears still streaking down his face, and she feels awful for hurting him. With a timid hand, she strokes his cheek, brushing his hair off his sweaty forehead, and watches as the salty liquid leaks from the edges of his clamped shut eyes. “Jared, baby, talk to me. Are you okay?”

His hazel orbs fluttered open and he gives a watery grin. “I’m okay just more intense than I was ready for.”

Gen sighs in relief that she hasn’t hurt him and she returns his smile before caressing her lips against his. “I’m glad you are alright, baby. I’m gonna clean us up okay, then we can talk, cuddle, and get some rest.”

Jared nods against the pillow he’s resting on. “Okay, Mommy.”

“Call me Gen, now, baby. Mommy time is over. You need wifey now.”

He chuckles softly, “Yeah, I do. Thank you for tonight, Gen. I needed that.”

She smiles and smooths a kiss over his damp forehead. “I know you did, baby. I know you did.”


	7. Primum Tempus

**Summary for the Chapter:**

> After meeting Sam’s girlfriend at his high school graduation, the reader is sent into a heat that only her true mate, Dean, can satisfy.

There was a great perk to having a beta for a boyfriend and that was to have someone quell your heats without any risk of having pups. That’s why when your next door neighbor Sam Winchester asked you out your senior year you said yes.

It was well known that an omega’s first heat happened around the time they came of age at 18 and for you it did 3 days after your birthday. You had already lost your virginity to Sam so when you called him over that first time he’d come straight away.

As a beta he couldn’t knot you and an alpha’s knot was what your body was craving. Despite your body’s need, you still would invite Sam over, tear at his clothes till you could sink your slick soaked cunt down his length; fucking him off and on until your heat died away.

This worked out perfectly for both of you until his brother Dean came home to see his baby brother graduate. Dean was living a few towns over working for a local garage and taking engineering classes at the University of Kansas.

In the time you and Sam had been together, you had only ever heard stories about Sam’s older alpha brother, but had never met him. Sam was excited for you to meet him and he drug you over to say hello right before your graduation ceremony.

Sam laced his fingers with yours and introduced the two of you.

The overwhelming scent of alpha washed over you, musky, smoky, a hint of leather and spice. An involuntary whimper climbed up your throat as Dean’s olive green eyes roamed over your face and body.

“It’s nice to finally meet Sammy’s little omega. I swore he was just making you up until now.“

There was a thick gravel to Dean’s voice and you felt a flicker of desire start low on your belly. “No, I’m very real. It was nice to meet you but we should probably go though. Need to get in our gowns and get into position.”

Dean gave an almost predatory grin before slapping Sam on the shoulder and walking away to find John and Mary in their seats.

Sam had walked back with you asking a bunch of questions about if you liked his brother or if you’d thought it would be worth hanging out with Dean sometime. He kept talking but you weren’t really listening. The familiar gnawing at your insides, that burning hunger, that need for an alpha knot was growing with every passing second. Something had triggered your heat and as you sat waiting for your name to be called to get your diploma, you realized it had to have been Dean. The lingering scent of virile alpha still clung in the air and when you looked over to where he was seated you knew he could smell you too.

His jaw was clenched and your eyes followed the strong lines of his arms down to his hands. You could see them pressing and rubbing at the bulge in his pants, trying in vain to bring himself some relief.

The sight made slick coat the inside of your thighs and you were thankful for the black gown you wore. A fine layer of sweat covered your body and you had never been more thankful to hear your name called in your life.

You rushed out of your seat, onto the stage to receive your diploma, and dashed back hoping that the ceremony would end sooner so you could go home with Sam. It felt like forever but finally it was over, caps flying in the air as you made a beeline for Sam.

“Hey baby, are you okay?”

You shook your head and bit your lip as a cramp so intense it almost made you double over while it wracked your body. You’d never had pain like this before and a strong whiff of alpha made the pain double and a gush of slick run down your thighs.

“I have to go Sam. Please, we need to go. I need, fuck!”

You had turned and ran right into Dean’s chest, a burst of his scent filling your lungs and making you whimper in need.

Dean growled as the thick aroma of your heat invited his senses.

Being this close to one another made it next to impossible for you to deny your attraction and it was Dean who took charge of the situation.

He wrapped his thick fingers around your wrist and looked at Sam when he spoke. “She’s in a full blown heat. She needs to be claimed or she’s gonna die. Why haven’t you claimed her yet Sam?”

Sam mouth gaped like a fish never having even thought about claiming you.

“He’s not my alpha. I’d only take a claim from my alpha, my true mate.”

The heavy weight of your words hung between the three of you and it took the presents of John and Mary as well as your own parents to break up the tension. It was clear to everyone you had come into heat and your mom wrapped her arm around your shoulder and guided you back to the car before taking you home.

* * *

For three days you suffered and it didn’t matter if Sam fucked you or not, your heat just raged on. By the fourth day, you couldn’t handle it anymore and you grabbed for the phone to call next door.

Dean answered on the third ring and you breathed a sigh of relief that he was still there.

“Dean,” you panted.

“Y/N, are you okay?” Dean’s voice sounded thick and husky, a rivulet of slick running between your thighs passed the soaked cotton of your panties.

“No,” you whined. “Need, fuck, need you. Need an alpha, I need you.” You groaned as another wave of pain scorched through your feverish body.

“What- what about Sam? Have you two tried…”

“It’s not enough. He’s not enough. Need an alpha, need you and your knot. Please Dean? Please help me?” You were begging, you knew you were but you had become desperate, and you panted harshly as you waited for Dean to decide.

“This is fucked up but, yeah okay. I’m coming right now. Fuck Sammy’s gonna hate me.”

“Hurry,” you whimpered and the click of Dean’s end of the call ending made you hang up the phone.

Your parents weren’t home, thankfully, and you made your way downstairs to unlock the door. A sturdy knock on your front door hurried your steps, and you could smell alpha before you even opened the door.

“Jesus Y/N, I could smell you from halfway across the yard.”

You barely let Dean finish his statement before grabbing him by his shirt and dragging him inside your front door. Pulling his sinful lips down against your own as he kicked the door closed behind him. Your arms wrapped around his neck, nails raking through the hair at the nape of his neck as he nipped at your lips and growled low in his throat, a gush of your slick dampening your ruined panties once again as he walked you towards the stairs.

Dean pulled out of your kiss, his hands coming up to cup the sides of your face as you reached the bottom of the staircase.

“You’re sure about this? I don’t even really know you, just what Sammy’s told me over the phone.”

You licked at your lips, his calloused thumb swiping over your lower lip and you pursed them together to kiss the pad of it.

“I’m sure. I need you Dean. I know we only know a little about each other but I also know that one lungful of your scent and I ended up like this. I need you to take me upstairs and mate me. Need you to knot me until this goes away. It’s been days Dean and it’s not getting any better. Please.”

The green iris of Dean’s eyes seemed to almost glow as the orbs shifted back and forth searching your face; his pupils dilating just before he crashed his mouth against yours again.

“Which room is yours?”

You broke the kiss and grabbed Dean’s hand, so much larger than your own, but still a perfect fit. Climbing quickly together until you reached the second floor and Dean anxiously followed you into your bedroom.

He shut and locked the door, not sure when your parents might come back but he figured they wouldn’t want to walk in and see the two of you knotted together.

Dean turned back towards you, finding you already sprawled across your bed. His eyes raked over your frame, your breasts poking out of the top of your tank top with every panted breath and the panties you wore had a dark wet patch across the strip that covered your core.

Kicking off his boots, stripping out of his shirts, and pants before moving towards the end of the bed. In just his boxers Dean slowly crept onto the bed, kneeling at your ankles, leaning forward on his hands to get a deep breath of your scent.

“God you smell good. Sweet like cherry pie. Bet you taste good too. Can I taste you Y/N?”

Your heart raced with Dean’s words and you nodded frantically at his question, lifting your hips to let him pull the drenched material down your thighs to discard behind him.

Full lips grazed over your soaked folds and you whimpered to urge Dean on, needing more, and he pressed his tongue between the lips of your pussy to lap at the slick you were covered in.

A deep, hungry growl left Dean’s throat, the vibrations rattling through your body, a sudden orgasm washing over you making your pussy clench around nothing.

“Please Dean, I need more. Need you and your knot. Please alpha, I need you.”

Dean sucked your clit into his mouth, his hungry for you still unsatisfied, and he lapped his tongue at you until you came arching off the bed again.

“There’s a good little omega. I need you to be nice and wet for me.” Dean pushed his underwear off his hips, kicking them off his legs as he crawled up your body, lifting the edge of your shirt, nipping at your overheated flesh and making you pant with need as he pulled the damp top over your head. Your legs spreading wider to make more room for him and an extra rush of slick dripped out of your core as the head of Dean’s cock brushed over your slit.

“Please alpha. I need you.”

“I know omega, I know. You ever had an alpha’s knot inside you before?”

You shook your head. “No, but I need you so bad. Mate me Dean, fuck me with your big cock, and knot me.”

Dean slowly nudged just the head inside you, a mewl of pleasure sounding from you.

“Okay, just relax Y/N. I got you.” He thrust slowly in, a rush of pleasure enveloped both of you immediately as he bottomed out.

“Fuck, you really haven’t had an alpha before have you?”

“No,” you squeaked as Dean pulled back and slammed back in, his cock rubbing your walls in ways Sam had never be able too.

“Guess I get to be your first then.” Dean kept a quick rhythm. The scent of your heat hanging thickly in the air around the two of you and drove him to mate you as fast as he could.

A thrum of pain rose through your body and you called out for Dean to knot you again. You needed it so intensely that the thought of not having it was too much.

“Gonna cum when I knot you my little omega? Feel your slick gush all over me.”

“Yes Dean, please. Knot me now, claim me please. Mark me as yours.”

Dean felt his knot start to swell and it trapped him deep inside you as he pumped out thick ropes of cum. He clenched his jaw however to keep himself from claiming you.

“Can’t claim you or you’ll end up stuck with me and a litter of pups for the rest of your life,” he ground out but you barely heard him over the rush of your orgasm, Dean’s warm cum splashing against your womb.

The high your orgasm sent you on lasted longer than any you had ever had before and Dean rolled to his back to let you lay across his chest while you waited for his knot to go down.

“You didn’t claim me.” It was a simple statement and Dean moved a chunk of your hair out of the way to look down at you.

“No, I didn’t. I couldn’t get you stuck with an alpha like me. I’ll just help you out with this heat and then you can find an alpha worthy of claiming you.”

“You are worthy Dean. If you weren’t, I wouldn’t have gone into heat.” You sat up, feeling Dean’s cock shift slightly and another ripple of pleasure moved through you.

He licked at his full lips, settling his hands to run up your thighs, and along your sides. Shivers ran down your spine at the soft caresses and you grabbed his hand to bring up to hold each of your breasts in his large hands.

Dean rubbed the pads of his thumbs over your erect nipples, your hips rocked over his still engorged cock lodged inside you, your eyes fluttering shut at the wave of pleasure it caused.

He gave a soft grunt, his hands moving to your back and pulling you down to claim your lips again. “Gotta let me come down first omega or I won’t be able to stop myself.” He growled against your lips, his tongue pushing into your mouth as you let out a moan and ground down on his again.

Another burst of slick flooded around Dean’s cock and his knot deflated just enough to allow you to move, sitting back up and canting your hips down towards him with short quick thrusts.

“Fuck, guess it was too much to hope it would work in one try, huh?”

You planted your hands firmly on Dean’s wide, firm chest and started to speed up your thrusts, bouncing up and down along his length, listening to his little growls of pleasure driving you towards another climax.

The feel of your nails digging into his flesh had Dean quickly starting to swell again, your slick cunt gripping at him furiously as you got close had him reaching to pull you down flush against his body again. His heels digging into your mattress and fucking himself up into you till his knot fully swelled for the second time, his resistance failing him this time as he sank his teeth into the crook of your neck claiming you as he pumped you full of his cum.

Blinding white flashed in front of your eyes, the pain for Dean’s claiming mark setting off sparks of bliss throughout your body as you came, violently shaking as your pussy clamped down over his cock till you were spent.

You collapsed onto Dean, his tongue gently lapping at the bite mark on your shoulder, and pressing kisses to your sweaty skin. It was so hard to stay awake this time but you managed to mutter a thank you to Dean before slipping into a restful sleep.

When you awoke several hours later, you were still on top of Dean, his cock having slipped free but his arms remained snug around your waist. You slid off to Dean’s side, a dull ache between your thighs and on your shoulder but no gnawing feeling in your stomach anymore to mate. Dean had successfully ended your heat and you snuggled back into his side as he continued to sleep thinking about what you might name the pups you were probably carrying now.

The conversation you had with your parents later that night was tense but not as tense as the one you had with Sam. He was hurt but after seeing the claim on your neck along with the faint smell of claimed omega coming off of your skin, he knew he had to step aside.

You felt bad for hurting Sam like you had but you couldn’t help the pull you had towards his brother. The smile that lit up your face whenever he was near and how overjoyed you were when you called him a month later to tell him he was going to be a father.

By fall you were standing in your new kitchen, a box of dishes sitting on the countertop as you put the glasses away in the cupboard in front of you. Heavy boots sounded behind you, followed by the thud of a heavy box of more dishes being set down on an open counter.

Dean wrapped his arms around your waist, his large palms caressing the swollen expanse of your belly as one of the two pups inside you pushed against it.

“How’s it coming in here?” Dean nuzzled his face into your neck, his lush lips grazing your mark as you moved your hands to cover his on your belly.

“Good but you are kind of distracting me.”

Dean laughed and pressed a kiss to your skin. “Wouldn’t be the first time I’ve done that.”

“Yeah I know. First my graduation, the reception at our wedding, when we were house hunting, packing my stuff, your stuff, and now this. Yeah, you are the king of distractions.”

You turned in Dean’s arms, your belly trapped between you as you leaned up on your toes to kiss your husband, your alpha, and your true mate.


	8. Dirty Deanna

**Summary for the Chapter:**

> To get into the fraternity Dean is pledging for he has to do a bit of gender bending.

With one final swipe of the mascara wand you were done and you leaned back to inspect your handy work.

“Okay, you can open your eyes. Wow, eye liner would have made your eyes pop more but just the mascara is fine.”

“Yeah right, like I was gonna let my girlfriend put anymore fucking makeup on me. No thanks. This is enough.”

You let your eyes do a final sweep of your boyfriend’s makeup before leaning down to kiss him. His plump lips tasted like cherries and you wiped at your lips with your thumb to remove the lip gloss he had left there.

“You look great babe and you need this for your pledge party tonight. Now get dressed, I’ll wait outside for you. Holler if you need any help.”

You squeezed Dean’s flannel covered shoulder before turning to exit the bathroom you’d been using to apply his makeup.

Dean Winchester had been your steady boyfriend since your junior year of high school. You’d gone to prom together, lost your virginity to each other, and now went to college together. Everything was perfect and with your recent admittance into Alpha Chi Theda it was only fitting Dean pledge for Sigma Epsilon.

Tonight was the annual Gender Bender party held at Sigma Epsilon and it would be the last before Dean’s house voted on making him a full fledge member of the frat or not. You hoped with all the hard work you’d put into getting Dean ready tonight he would make it in.

The door to the bathroom finally cracked open a few minutes later and when Dean stepped out you bit into your bottom lip.

“If you fucking laugh I’m asking for my ring back.”

You clutched protectively at the promise ring on your left hand and took a deep breath before responding.

“I wasn’t going to laugh I was just going to ask why you shaved your legs.”

Dean looked down at his hairless legs and tugged at the ends of the denim skirt he wore.

“Hairy legs on a chick in a dress is gross. If I gotta wear a fucking skirt, I’m going all out.”

You strolled over to your boyfriend, his hands fidgeting with the buttons to the white blouse he wore.

“Babe,” you ran the palm of your hand over his arm, a part of you regretting not putting him in a tank top instead to show off his arms. “You look fine. Hot even.”

Dean crooked a brow at you when mentioned the word hot.

“What, you do. It’s not like it’s a fucking secret, I like chicks too. This is just best of both worlds.”

Your arms wrapped around Dean’s neck and his hands settled on your waist as you gazed up at him. Sparkling shades of rusty brown eye shadow dusted his lids and the dark mascara made his already long lashes look longer, framing his emerald eyes perfectly. The rosy hue of his cheeks and his cherry pout was enough to take him for handsome to drop dead gorgeous.

“You make a pretty fuckable woman Dean. Maybe after the party tonight we can come back here and you can leave lipstick kisses all over my body?”

Dean smirked, “sure babe. Just make sure to call me Deanna when I make you cum on my cherry red lips.” Dean smacked his hand against your ass and pulled out of your embrace to walk towards your bedroom door, his black leather cowboy boots thudding on the hardwood floor.

“You coming sweetheart, or what?”

You shook your head to get out of the fantasy you had been lost in of Dean and his cherry glossed lips.

“Oh yeah, I’m coming babe, sorry. Just your fucking mouth is distracting in that colour. Like it wasn’t a huge problem before.”

You scoffed and grabbed your jacket off the back of your desk chair before following Dean out of your room, and to the party that would determine Dean’s fraternity future.


	9. Pups for Mother's Day

**Summary for the Chapter:**

> Waking up on Mother’s Day in heat has you deciding its time to finally become a mom yourself with your true mate Dean.

Hot, achy, and slick; this was not how you had planned to spend Mother’s day. You had planned on going to see your mom, taking her out to lunch, and getting your nails done together which was your usual tradition. But as you awoke, your body feeling like it was on fire, a burning need to mate clawing at your insides, you knew your plans for the day weren’t gonna happen.

You opened your eyes slowly, taking in the sight of your husband, your alpha, Dean staring back at you. His jaw was clenched and you knew the scent of your heat had woken him up.

“Morning my omega,” he practically growled and you smiled. Even after being married and mated for the past three years, Dean still had a hard time completely controlling himself when you had your heats.

“Mornin’ alpha,” you purred and moved to snuggly closer to him. You head nuzzling under Dean’s chin as he wrapped an arm around you to pull you into his chest.

“Guess plans with your mom today have to change.”

“Mmm,” you hummed taking deep breaths of your alpha, the spicy musk of leather, motor oil and whiskey filling your lungs, and making more slick run between your thighs.

“Did you want me to go out today? Let you coast through this one like last time?” Dean’s hand ran up and down your back, your nerve endings bursting with heat at every touch as he pushed under the hem of you t-shirt.

“No, stay.” You leaned up to nip at Dean’s jaw, the prickly hairs of his scruff tickling your lips as you kissed over it to his lips.

“Need you to stay. Need you to mate me. Like we talked about.” Your lips collided with his, your hands pushing on his bare chest, Dean rolling to his back and letting you crawl to settle on top of him.

Dean licked his way into your mouth, his hands pressing down on your hips to rub you against the erection in his boxers. The soaked material of your panties leaving a smear of arousal over his covered length.

He rutted against you, the wet cotton of your underwear rubbing deliciously over your clit sending sparks through your core. You cried out into Dean’s mouth as an orgasm washed over you. They were so easy to achieve when you were in heat and Dean was happy to take advantage of that.

As the wave of pleasure started to ebb away you pulled away from Dean’s mouth to sit up in his lap, reaching for the hem of your shirt.

“You sure you wanna do this Y/N?”

Your shirt came up over your head and you threw it behind you to land carelessly on the floor.

“I’m ready Dean. I want pups. I want to be able to celebrate Mother’s Day next year as a mom. I found my true mate, my soulmate, and I want to have pups with my alpha. Mate me Dean, please?”

He licked over his plump, pink lips, a look of hunger filling his eyes, and he reached up around the back of your neck to pull you back down into a kiss. His chest pressing hard against your breasts as he rolled the two of you over to put himself on top.

“My omega wants her alpha to fill her up with pups huh?” Dean kissed and licked down your neck, his lips grazing the raised skin of your claiming scar, and making you shudder.

“Yes alpha, please. Need you to knot me.”

Dean growled into your skin, his teeth nipping your bare shoulder as he trailed his mouth down to your chest to take a nipple into his mouth. Sucking greedily at the puckered flesh, teasing his tongue over it before moving to the other breast, and lav it with the same amount of attention.

Keening like moans fell from your parted lips as you tangled your fingers into Dean’s hair and tugged as he pulled your nipple roughly with his pursed lips. Your hips canted towards Dean, a failing attempt to get more friction on the searing need in your core.

He moved his hands down your sides to press into your hips and hold them down on the bed. With long lickes of his tongue, Dean moved down your body, pressing a kiss just below your belly button before tangling his hands in the sides of your drenched panties.

“Please Dean.”

“Soon my impatient omega. I’ll fill this belly with pups soon enough. Just want to taste you first.”

You let out a whine as Dean pulled your underwear off your hips, down your legs and discarding it off to the side of the bed to the floor. A wave of arousal coursed through you as you watch Dean lean down to breathe in your scent. His scruff scraping along your inner thighs as he nuzzled into your pelvis, his tongue swiping over your wet slit with a groan.

“Alpha,” you cried as Dean again flicked his tongue out between your folds, catching it on your engorged clit.

He licked and suck at you, his hunger for you increasing with every breath he took and lick he made over your dripping cunt.

Need burned in your core and like a shot another orgasm overtook you, Dean lapping at your pussy as it clenched around nothing.

“Alpha please. I need your knot, need to feel full of your pups. Please, Dean. ”

Dean kissed at the swollen lips of your pussy, your hips thrusting towards him with a whimper of need.

“Poor little omega, so desperate for my knot.” Dean slowly crawled up your body, the sight graze of his chest over yours making you mewl and reach for him, fingers digging into his back.

He kissed your lips gently, his hand coming up to cup the side of your face before pulling away to look into your eyes.

“You’re sure this time?”

You nodded and a dimple inducing smile transpired on Dean’s face.

“Okay,” he whispered. “Turn over sweetheart. Have to do this the right way.”

You smiled and Dean moved back, kicking his boxers off as you turned onto your hands and knees; presenting yourself.

Dean cursed behind you as the scent from your heat permeated the air more heavily every second you stayed in this position. His hands gripped your hips tightly and with practiced precision the head of Dean’s cock sank into your slick cunt; pushing in till he bottomed out.

As much as you wanted Dean to pound into you, fuck you quickly into oblivion, you knew to successful be knotted by your alpha he had to take it slow. Long, languid drags of Dean’s cock along your slippy walls made you shudder, his thick length filling you deliciously with every push in of his cock.

Dean drew himself over your back, his chest covered in sweat, hips pushing against yours as he kissed the back of your neck. His hands drifting slowly across your belly and between your thighs his middle finger slipping through the cleft of your pussy to press on your clit.

Your body jerked at the contact and you pushed back against Dean.

“So close omega. Can smell you and how badly you want my knot. Tell me Y/N. Tell me,my pretty omega. ”

“Oh Dean, alpha. I need your knot so bad. Please alpha, knot me. Fill me up with your pups.”

The finger pressed to your clit rocked with every solid thrust and Dean tilted his head to lick over your claiming scar, his teeth grazing it as you felt him start to swell. The beginning of his knot sending you over the edge, fluttering and squeezing, your body flushing at the ripple of pleasure.

As you started to come down, Dean dropped his hand from between your legs, and onto the bed. His hips snapping more quickly now, his tongue licking over your scar one more time before biting down, his knot thickening as he released load after load of his cum deep inside you, his knot locking him in place.

The feel of your alpha’s knot and his warm cum splashing over your walls had you cumming again, the pain from your claiming scar being broken open had you crying out in intense pleasure.

Your cries turned into slight whimpers and Dean licked and kissed over the reopened wound, gently lowering the both of you to the bed on your sides as you waited for his knot to go down.

“Sorry,” Dean murmured pressing another kiss to your mark.

“It’s okay. All part of the process, right? If I want pups we have to do it right. You think it worked?”

Dean nuzzled into the back of your neck, his hand sliding over your hip to rub over the space under your belly button.

“We’ll know in a couple hours if you get hit with another wave but I think this one was the one. Never cum that fucking hard in my life and it was all for my omega. Love you Y/N.”

You turned your head and Dean leaned over the best he could while still lodged inside you.

“I love you too, Dean. My alpha.”

Dean softly kissed your lips before snuggling back down behind you to get some rest and wait to see if it took the first time. He hoped so, his dreams full of images of you round with pups and chasing small children around a playground; his omega, his soulmate, and hopefully mother of his pups.


	10. Sweet N' Tart

**Summary for the Chapter:**

> Claire Novak needed someone to be the missing father figure in her life and Dean is happy to fill that roll. From Dean’s pov and just know this doesn’t have the happiest ending.

She was too young, my best friend’s meat suit’s daughter. She was danger and bitterness that tasted sweet like strawberries and tart like lemon. It was clear that she was trouble, looking for someone to play daddy, and fuck if it didn’t make my cock as hard as steel in my jeans.

During the day she would whine, drive me up the wall as I tried to teach her how to be a better hunter; but at night her voice seemed to drop, husky and warm like molasses as my name rolled off her tongue. She’d make these purring noises like a cat, my fingers tugging at her blond hair as she’d suck me off.

God, she had a mouth built for sin and her tiny hand would always gravitate between her naked thighs, fingers burying deep in her shaved bare cunt when I’d gag her with my cock. She’d fuck herself on them while I fucked her mouth, her juices running down her hand and thighs to puddle at my feet every time.

Without fail, Claire would beg for me fuck her, to take her rough from behind, my hips making bruises against hers as I pulled her back by her shoulder.

“Harder, daddy…” she’d always moan and I’d flip her over, flat on her back, blue eyes wide as I fucked her straight down into the comforter. The thumb on my right hand pressing hard on her clit as my cock pounded into her, going so deep my balls would bounce and slap off her tight little ass with an almost stinging force.

I’d grab her small tits, squeezing them, watching the way they disappeared under my hand, pinching those sweet, pink nipples, tugging on them while she cried out underneath me. Fuck, she loved this more than I did, and she was always so willing to accept my release of pent up tension.

I’d fuck her hard and fast, her pink tongue wetting her lips and filthy moans sounding from her mouth. Jesus, there wasn’t anything about this girl that didn’t scream naughty little girl.

Her tousled blond locks and eyes with coal smears around them made her look even younger, and that’s when the guilt would set in. Cas’ words ringing in my head, thanking me for looking out for Claire.

“What’s the matter, daddy? Need your big cock to fuck me harder. Need to cum on your cock and have you cum on my tits.” Claire rolled her hips against me and her voice drowned out the ones that made me feel guilty.

“My baby girl think she’s been good enough for daddy for her to cum?”

“Yes daddy, please. Wanna cum on your big dick,” she mewled obscenely.

Fuck this girl knew how to push my buttons, and I fucked her hard till I felt her pussy clamp down around me, that sweet little cunt becoming impossibly tight, my jaw clenching as I struggled to stop myself from cumming inside her.

We knew the risk if I didn’t pull out in time, besides, she liked it better when I came on her, painted her milky skin with my thick cum. I fucked her through her orgasm, her little hands clawing at my shoulders before I felt my balls tense and draw up. I pulled out to fist myself over her stomach, cum spurting over my fingers, landing on her stomach and chest, marking her in my jizz.

I’d always sit back on my heels to watch her, knowing her slender fingers would run through the mess on her body, that perfect little tongue of hers licking my cum from her body one finger full at a time.

* * *

It was always like this with us. I was the daddy she needed and she was a good lay after a stressful hunt, her petite body easy to manhandle when I needed it. But it wasn’t always like that, and it often makes me wonder if I should cut her off and end whatever this was.

She’d been so shaken, her sapphire eyes watery and full of concern after a ghoul tossed me across the room. I was fine and I told her as much but when we’d gotten back to the bunker and were finally alone with each other, she’d fucking lost it.

Claire ripped at our clothes and sucked greedily at my bottom lip, all of her movements letting me know she was in control. She’d pushed me down and climbed to straddle me, her pussy already dripping, and my cock hard from the lingering adrenaline of the hunt.

She sank down slowly, a deep breath released from her steadily as she settled, her hips flush against mine and all of me stuffed up inside her warmth. God she was tight this way and it took me thrusting up into her to get Claire to move. She moved slowly at first, rocking her hips, my hands settling on her waist to thumb over her smooth skin, her own hands grabbing my forearms to help her remain upright.

Her pace was slow, so much slower than our usual quick, hard fucking, a sure sign that things between us had changed. The nails on her hands raked down my arms as she lowered herself to my chest, her mouth molding with mine. Finally, I was in a position that I could fuck myself up into her.I needed the friction and this slow pace was way too loving for my liking and for what we had going. Pounding up into her made her bounce on top of me, her nipples rubbing over my chest into stiff peaks and those little breathy moans she always made started to fall from her lips.

“There’s my girl.” I mummered into her mouth and she pulled back again to sit up.

Planting her hands on my chest she rode me, her breasts bouncing in time with her body and I reached up to fondle them, squeezing the small mounds and thumbing her nipples. She looked like teenage sin like that, bouncing and fucking herself on my cock, and I decided maybe letting her have a night in control might be fun every once in awhile.

I met her thrust for thrust and when she threw her head back, blond hair flowing down her back, I knew she was close. I wrapped my arms around her back, pulling her down flush against me again, one hand moving to squeeze her ass while the other fisted in her soft hair.

“Cum for me, little girl. Let me feel you cover my cock in your cum. Squeeze my dick, baby girl.”

A slightly frustrated moan came from her and she rocked down hard seeking her end.

“Want you to cum, too.”

I sucked just under her ear, feeling her shudder and clench around me. “I will, baby girl, after you cum I’ll let you suck up every last drop.”

She shook her head and pulled back to look at me. “No, I want you to cum inside me. Please?”

God she was whining, and I reached for her face to kiss her. “Can’t, you know that. Be a good girl and cum for me. Cum for daddy.”

Her blues eyes locked with mine and she rode me hard till finally her walls started fluttering, a gush of slick coming from her as she came crying out my name. She kept moving though, and I felt myself getting to that point where I need to stop and pull out, or just fucking risk it.

Claire seemed to notice, mewling like sounds coming from her, and her cunt became impossibly tight around me.

“Fuck, Claire I’m gonna fucking cum. Fuck!”

“Cum inside me Dean, please.”

Jesus, the way she said my name and how wet and tight she was had me letting go. I pumped my hips up into her and filled her up. It was probably the second stupidest thing I’d ever done with the girl, but fuck it was nice to finally cum inside a pussy without a fucking condom in the way.

She curled up on my chest as I panted, trying to remember the proper way to breathe, when she said the words I’d always dreaded to hear from her.

“I love you, Dean.”

And just like that I was hit with a wave of icy panic. I pulled her off of me and dumped her down next to me on the bed.

“That ain’t- Claire, you don’t love me.”

“Yes I do, Dean. Did you think this was just sex? I love you.”

I reached over the side of the bed to grab for my boxers and pulled them on quickly. “Yeah Claire, it fucking was just sex. You’re my best friend’s daughter.”

“Castiel is not my father!”

I pulled her shirt up from off the floor and threw it at her. “No, but he sure does protect you like he is, and I’m not going to fall in love with his kid. It was just sex, Claire, and obviously you’re too young to realize that’s all this ever was and all it ever will be.”

She pulled her shirt over her head and looked up at me, mouth parted with glimmering tear filled eyes that looked just like her father’s.

“I thought we had something. It’s why I wanted you to finish inside me. I love you and I trusted you and I thought I was gonna lose you today. I-” she admitted, shuffling off the bed after a long moment of thick, tense silence. Claire wiped at her eyes, smearing her eyeliner over her cheeks. “I- no this is stupid. I’m stupid. I’m gonna go.”

Fuck, this wasn’t good at all.

“Claire, wait. Come on kid.”

I walked around the bed and grabbed her by the arms, stopping her from pulling on anymore clothes.

“Claire, stop. Hey, look at me.”

A set of teary blue orbs met mine and her chin quivered as she tried to not let anymore tears fall.

“Hey, I’m sorry okay. I didn’t know this was more for you but Claire, I’m not in love with you. Honestly, I could never fall in love with you. You’re too young.

“I’m 19.”

“Exactly, too young for me. I’m almost 40 Claire. I could almost legally fucking drink by the time you were just learning to hold your head up. I’m too old for you, and I’m never gonna be in love with my best friend’s kid or charge or whatever. I’m sorry, Claire, but all this will ever be is sex.”

“I hate you.” She shook herself from my grasp and finished pulling on her jeans, storming out of my room and to hers at the end of the hall near the kitchen.

I fucked this up, bad, but I knew I could at least try and fix it. I got dressed and grabbed my keys, heading into town to see if the pharmacy was still open. It was and after getting a pack of morning after pills I snagged a few bags of Hot Cheetos, a few Twix and a two liter of Coke to take home; all the junk food I knew Claire liked.

This wasn’t going to go well but I knocked on her door anyway, and when she told me to fuck off and go away I let myself in.

“Look kid, I know you hate me right now but you need to take these. Cas would kill me if you got pregnant. And I got you some of your favorite junk to eat cause the guy at the pharmacy said it might be helpful to have some comfort food after.” I put the bags down on the end of the bed and she just shook her head scoffing at me.

“Really, that’s how you say I’m sorry. Have some Plan B and Coke. I fucking hate you. God, fuck you Dean! No wonder no one has ever loved you and stuck around. I’m gonna call Jody and see if she’ll take me back in. I can’t be around you. Get out.”

“Just take the fucking pills alright.” I stormed out of her room and down to the library to fix a drink. By the next afternoon Claire was gone, and back at Jody’s.

* * *

“I’m not sure what happened between you and Claire but I still want to say thank you Dean. You tried to make her a better hunter and I’m sure you did your best.”

I gave Cas a half-hearted smile and drained another glass of it’s contents. I was gonna need more whiskey soon if Cas kept thanking me. If only he knew that Claire left because I was screwing her but wasn’t willing to love her back. God, I’m a piece of fucking shit.

“Yeah, something like that.”

* * *

Three months later Jody called Sam to ask if we had seen Claire. She’d taken off and we hadn’t heard a word from her since before she had left. Cas looked but he couldn’t get a read on her, we figured she had figured out how to use some angel warding to keep him away. We searched for a long time, even asking other hunters to keep an eye out for her, but nothing for almost 3 years.

Finally it was late in the fall, almost Thanksgiving when we got another call from Jody inviting us to have dinner with her, her new husband Joe, and Alex. Sammy and I had made the drive up to Sioux Falls and were surprised to see a tiny red sedan parked in the driveway as well.

“Alex get a new car?” Sam asked as Jody answered the door to let us in, and she just shook her head and laughed.

“Nope, even better. Someone finally decided to come home for Thanksgiving.”

We followed Jody into her living room, and there on her couch was Claire. Hair pulled back behind her ears and not a stitch of makeup on her face. She was laughing, and when I turned my head to see what was making her laugh I felt the air in my lungs evaporate.

Alex was pinned on the floor by a tiny little girl with dirty blonde hair, and when the little girl looked up at me it was with eyes that I’d seen millions of times in the bathroom mirror.

“Hey guys, look who finally showed up so we can eat!”

I felt sick, and when Claire’s eyes shifted to mine then down to what had to be her kid, I turned around and bolted for my car. There was no way this was happening. I had found the empty pill packet in the trash can in her room; there had to be some mistake here.

Claire had followed me out to my car, her still too young, still too small hand grabbing me by the arm to stop me from getting into the Impala.

“Dean, wait. We need to talk okay. It’s not what you think.”

I turned to face her, swallowing down the bile I felt rising up in my chest, and licked my suddenly dry lips.

“Not what I think. Claire you’ve been gone for three years and you show up with a kid. A kid who looks like me. I saw the empty pill pack so I don’t understand how that little girl is even a possibility.”

Claire smiled and it wasn’t the broken one she had always had when she was around those few years ago.

“Dean, Amelia isn’t yours. She’s my husband’s.”

“Your husband’s?”

She laughed and I felt like a 10 ton weight had been lifted from my chest.

“Yeah my husband, Austin. I met him on Tinder just after moving back in and he’s the reason I took off. We dated for a few weeks and then got married in Vegas. Amelia is one and a half. She’ll be two after Christmas. She isn’t your daughter Dean. I swear to you she isn’t.”

I nodded slowly letting it sink in and pulled my bottom lip in between my teeth.

“But her eyes?”

“She got from her dad. I have a type okay. Look, come back in and I’ll introduce you to Austin and Amelia. Hell, call Cas and have him get his feathery ass down here to meet Jimmy’s granddaughter.”

“Yeah, alright I’ll do that. I’ll meet you inside in a minute.”

Claire flashed me a smile, patted my arm and walked back inside. The kid wasn’t mine and I was glad for that, but somehow a part of me was just as disappointed as I was relieved.

I called Cas and he popped in for his first real Thanksgiving, we ate dinner together, and Austin turned out to be a great guy. His hair was a bit too long for my liking, but if I could put up with Sam’s mop top I knew I could handle this kid. He made Claire happy and would love her like I couldn’t.

As the night drew to a close Cas pulled me aside away from everyone saying goodbye in the living room.

“Dean, I’m glad to know Claire is finally happy and that she has someone like that Austin fellow to raise her daughter with. You would have been a good father to her too but it is better this way.”

“Cas, that kid ain’t mine.”

Cas nodded and patted my arm in the same place Claire had. “Indeed, she did say that. I must be going Dean. I left some very important things with Chuck that I really should be getting back to. Thank you for calling me.”

In a flutter of wings Cas was gone and I was left to wonder if the little girl Claire was buckling into a carseat was really mine or if she had been truthful when she said she was Austin’s.

I shook Austin’s hand, his grip firm in mine. “Take care of those girls, you hear me.”

“Yes sir, I definitely will.”

I let him walk out, stroll over to his wife and pull her in for a kiss before they got into their car to leave.

It was better this way. Even if she was mine, he would be a better man to raise her than an old hunter like me.


	11. Good Boy

**Summary for the Chapter:**

> Dean is such a good boy for his Mistress especially since its all about her pleasure over his.

Tonight was about her. She had control, and it was about her getting what she wanted. It was the terms I’d wanted tonight, her pleasure over mine, no talking, no touching, no cumming, not without her word. I’d get to watch her cum over and over until she was spent, denying my own pleasure and needs.

“Strip,” she ordered and I was quick to push my leather jacket off and discard my boots. Jeans and other layers pulled off and put on a chair in the corner. “Good boy. Undress me.”

I was careful, eyes downcast and focused on gently removing her top, unsnapping the clasp of her bra. I knelt at her bare feet, opening her pants and tugging them off with her underwear. A groan at her beauty escaped me and I bite at my lip to stifle it too late.

“Tsk, tsk, tsk, Dean. You know better.”

“Sorry Mistress.” My head drops and I stare at the beautiful crimson color on her toes waiting for her instructions.

“Stand up Dean and grab one of the toys from the middle drawer.”

The middle drawer, it held strapons and dildos of different sizes. I knew my mistress well enough to know which strap on was the best fit for her, but when I reached into the bureau drawer she called out to me.

“Dean, tonight’s about me baby boy, remember?”

“I remember, Mistress.”

She grinned fondly, “that’s my good boy. Put that one away and grab the black one that’s hallow. You get to wear that tonight.”

I released her favorite flesh colored dildo and reached over to the left, my fingers wrapping around the silicone fake cock. It had elastic straps, and I stepped into them diligently arranging each strap around the tops of my thighs.

My cock was already hard, bobbing in front of me as I moved the straps, and it was a bit of a struggle to fit inside the hollow opening but I managed; the thick and veiny textured dildo covering my length and resting against my taut sac snuggly. We’d never used this one before but I throbbed at the thought of filling my Mistress and giving her the pleasure she deserved.

“Looks so good on you, Dean. Lay on the bed for me baby boy.”

“Yes, Mistress.” I licked my chapped lips and walked quickly over to the king sized bed, it’s cool cotton sheets making me shiver as I laid back against them. My covered cock strained up towards my belly, leaking and aching inside the sleeve as my Mistress approached the bed and started crawling towards me.

“You doing alright baby boy? Comfortable?” She stroked a hand along my cheek, her skin so soft, so perfect and gentle.

“I’m good, Mistress. Thank you.”

She smiled and leaned back on her heels. “Such a good boy. You remember your safe word and gesture?”

I nod as I answer, “Yes Mistress. Safeword is salt and it’s two taps if I can’t speak.”

“Good boy. Thank you Dean. Be a good boy and eat Mistress’s pussy. I want to see that gorgeous face between my legs.”

“Yes, Mistress.” I moved only a fraction of an inch before her delicate hand touched my chest.

“No baby, lay back. If there was ever a face worth sitting on baby boy, it’s yours.”

My cock twitched at her words and I settled back, waiting for her to move over my face. Her beautiful cunt hovering over my waiting mouth, her thighs pressed softly against my ears. She grabbed the headboard for stability and lowed herself to my mouth, my lips brushing against her folds in a gentle kiss before probing her slit with my tongue.

A mewl of need fell from her parted lips and I grabbed the sheets knowing I couldn’t touch her, not without her words, her permission. I sucked at her swollen clit, tonguing at her opening, her sweet flavor coating my tongue, lips, and chin.

“Touch me Dean. It’s alright.”

I groaned into her cunt sending vibrations through her as I released her sheets only to grab her by the tops of her thighs, pulling her closer to my mouth, burying my face in her pretty pussy, feeling her grind down against me, clit throbbing against my tongue.

“Such a good boy. Gonna make Mistress cum. Make me cum baby boy.”

Like a man starved I devoured my Mistress’s pussy above me, flicking, swirling, and sucking on that plump little nub driving her higher and higher until she let go of the headboard and grabbed a fistful of my hair.

“Right there, Dean yes. Oh god, yes. Fuck!” She withered on my tongue and I lapped up her release, the muscle of my tongue coaxing every drop of pleasure from my Mistress as I could.

She let go of my hair and the headboard, crawling backwards down my body, a trail of her slick and my saliva coating my chest and stomach as she moved over me. “Such a good boy for me,” she panted. She grabbed my chin in her small hand and pulled my mouth to hers; tasting herself on my lips and moaning at the tang of it.

Wiggling down further, my hands slid up from her legs to her waist, as I settled her dripping cunt on the fake cock and my heavy sac. Her tongue traced my lower lip briefly before pulling away to sit up. Rocking slowly back and forth, drawing my gaze down between her beautiful shapely thighs, the lips of her pussy spreading over the black silicone, wrapping around the veined sides, and smearing her juices over the rubber.

She moaned wantonly as her clit rubbed over the length, wetting it with her arousal before reaching down to grab ahold of my cock, her fingers grazing the exposed skin of my belly, an involuntary growl rumbling in my chest.

“Calm down, baby boy. I still haven’t decided if you deserve to cum yet. Mistress still has needs. Hands off for now baby.”

I dropped my hands down flat on the sheets, waiting as she raised and slowly lowered herself onto the shaft. Instantly I missed her as I watched her bottom out, the warmth, the wetness, the softness of her walls around my cock. A whimper fell from my lips and I bit into my bottom lip, hoping my Mistress didn’t notice.

“I heard you baby. What’s wrong?” She rocked back and forth leisurely, her eyes fluttering as the cocks ridges hit that sweet spot inside her.

“I miss you, Mistress. I miss the feel of your pussy around my dick.”

She laid her hands on my chest, no doubt feeling the quickened beat of my heart at the contact. “I know you do, baby boy. But you need to be punished while Mistress get what she needs. The noises earlier can’t be forgotten, but if it’s too much baby just use your safeword.” She raised up and down, starting a bouncing rhythm on the fake black cock inside her, her nails digging into my chest and her breasts starting to sway before my eyes.

I wanted so badly to reach up and grab hold of the fleshy mounds, but heeded the words of my Mistress and tangled my fingers into the sheet, pulling them tight, and turning my knuckles white.

Sweat ran down between her perfect tits and I licked my lips as I watched it fall straight down her stomach. I needed to touch her but I kept still, fighting my urge to thrust up into her and help my Mistress cum.

“Dean, touch me baby. So close baby boy. Mistress needs to feel your hands.”

Her voice sounded completely wrecked and I took my time feeling the smooth skin of her legs, her waist, and up until I reached those beautiful tits. Palming them, feeling the weight of them heavy in my hands while she kept grinding. Thumbing over the purt peaks of her nipples, a moan fell from her beautiful pink lips, and I gave them just the slightest pinch to watch my Mistress fall over the edge.

There was the moment I was needing tonight, to see the bliss and satisfaction on my Mistress’s face. It was almost enough watching her ride that high to get me off too.

A brilliant smile lit her face as she came back to herself. She seemed to contemplate something before she started moving again, her pussy making a squelching sound around the dildo as she moved up and down it’s length, searching for another release.

I pinched and rolled her nipples, wishing to have them in my mouth and like she could read my thoughts she leaned forward, offering her breast to me. “Use your mouth baby.” She ground down on me, her pussy dripping onto my skin exposed around the fake cock. I reached for her nipple, resting my hands on her waist as I licked and sucked at her tit till she cried out, cumming again.

She leaned back away from me, a sated smile on her face. “Thank you, baby boy. You were so good for Mistress.” She raised herself off the rubber cock, letting it slap wetly against my lower belly. “Take it off Dean, Mistress thinks you should be rewarded.”

She climbed off my lap and I lifted my hips to work the straps off my legs. My cock had softened slightly, and as soon as the strapon was off my Mistress straddled me again. I stayed still waiting for her to decide what to do to me; my reward for being good just within reach.

“You did good tonight, Dean.” She wrapped her fingers around my bare cock for the first time that night and I moaned obscenely at the simple contact. “So wound up aren’t you baby?” She started stroking me, my shaft hardening immediately at her touch. “I’m gonna let you cum baby boy, just relax.”

She shifted in my lap, dragging my cock between her soaked plump pussy lips and I almost came as she rutted against me once. “Wanna watch you cum on my clit baby. You were so good for Mistress.” She rolled her hips and I felt my balls draw up tight. She knew how to get me close quick; feeling and watching her cup my cock while grinding her pussy against the thick vein on the underside, pushing me there fast.

“Mistress, may I cum?” I strained to hold back, my jaw clenching along with my hands in the sheets.

“Yes Dean, cum for Mistress, baby boy.”

There was no holding back and my hips thrusted up just as the first spurt of my cum released, hitting her clit and smearing over her cunt. She moaned at the feeling as I got lost in the euphoria of my orgasm.

When my cock stopped pulsing I stared transfixed at my painted Mistress. Her pussy, stomach, and the bottom slopes of her tits were coated in white and she brought her palm up to her mouth from my cock, licking it clean.

“Mmm, good boy,” she hummed in delight.


	12. Vanecila Nenipa

**Summary for the Chapter:**

> To gain the location of the Winchester’s the reader decides to try another method of interogation.  
> W

He had been hanging there for hours. His wrists trapped in tight leather bonds that stretched up on long chains above his head, the muscles of his shoulder blades ached and he was almost thankful that his clothing had been stripped of him as he flexed his worn wings. The movement relieving some of the tension. Castiel wished he could see however, the sound of heels on concrete drawing his attention away from the pains in his body as she entered the room. Kerry, his captor and today’s interrogator.

“Hello Castiel, are you ready to talk today?”

“No.”

He heard her sigh and followed her footsteps as she moved closer to him

“I thought you might say that. That’s why today we’re going to try something different.” The low sultry sound of her voice made a shiver run down his spine and he listened to her move behind him.

“I was thinking today instead of beating the location of the Winchesters out of you, like my fellow brothers have, I’d like to try rewarding you instead.” She leaned in close against his back, her breath fanning hot over his ear. “Tell me Castiel, do you like having your wings stroked?”

A set of warm hands touched his lower back, the fingertips running slowly up the expanse of his firm tanned skin till they reached his shoulder blades. Ever so slowly her fingers moved around the base of his wings, caressing gently as she pet over their silky down.

He tried to steel himself, ignore the sensations traveling through his body as her fingers ruffled through his feathers. But a shiver of pleasure shot down his spin and his once limp cock started swelling, quickly becoming so engorged it almost hurt to not have her touch him there.

“Does this feel good for you Castiel? I know having mine stroked makes my vessels pussy drip. Just standing here touching you I can feel myself getting wet.”

Her hands fell away from his back and disappointment rocked through him at the loss. He listened to her rustling around behind him and he sucked in a breath in surprise as a bare set of breasts pressed against his back.

Her hands settled on his naked hips, fingers tight on his flesh, the cool metal of her rings heating against his skin before her left hand inched over his hipbone towards the root of his cock.

He twitched uncontrollably as she encircled his weeping length, a shuddered sigh broke from his parted pink lips as she squeezed and release him. The delicious warmth of her grace skimming down his chest, paying only the slightest bit of attention to his nipples while she focused on his pulsating cock.

“Are you okay Castiel? Your cock is so hard, so full. Does it hurt? I can help you Castiel. All you have to do is tell me where they are.”

Cas gulped down a lump in his throat; he was unbearably aroused, but he could not betray the Winchesters like this.

“No,” he rasped.

She clicked her tongue and squeezed his cock again. This time stroking up and down his shaft, twisting around the damp tip and dragging the pre-cum down the velvet hard flesh. Her grace added to the sensations as his sac warmed from her grace-fueled fondling.

“That’s too bad Castiel.” Her movements sped up, her grace licking softly at his sac as a grunt of pleasure fell from him and his balls drew up, just on the verge of spilling over her first.

She stopped suddenly, hand releasing his swollen and needy cock, and her grace disappearing from his sac. “I’m sorry Castiel but you have to earn the right to cum.”

Cas dropped his head down, his chin almost touching his chest, the dark tie around his head making it impossible to see the floor he knew he would see if he could. He felt her shift behind him and gasped as her soft wet lips pressed to his back, kisses scattered over his skin until she met the base of his wings again.

Sparks shot through his body as he felt her tongue lick over the feather of his right wing. His length throbbing with every touch of her mouth to his feathers. “Fuck,” he cursed softly, her fingers stroking his left wing while her tongue licked just around the joint on his back.

His need for release was overwhelming as she licked over to the other joint. She sucked softly at the skin of his back, the tip of her tongue flicking up and over his wing, trails of saliva coating his plumage as she wiggled the wet muscle over and between them.

Her right hand gripped into his right wing, tongue swirling on his left as her breasts pressed firmly along his spine. The feel of her left hand creeping over his side, down his ribcage to settle just above his straining cock was too much. A guttural moan reverberated off the stone walls as Castiel threw his head back and came. Thick, white rivulets of his seed spurted from his cock landing on the cold concrete floor at his bare feet. The bliss Cas felt was short lived as she moved away from him quickly.

“Oh Castiel, it’s such a shame that you came like that I had plans to taste you, to bury my fingers in my pussy and let you lick them clean before moving you to a chair so I could strap you down and ride you. You could have cum in my vessels tight, slick pussy. That is if you told me where the Winchesters are. Maybe you want to tell me now and we can finish what I had planned?”

Cas lowered his head, wishing he could see the angel before him, look into her burning hazel eyes, take in the wild brunette curls around her face and watch her push up the her glasses along the bridge of her nose in annoyance when he gave her a resounding, “no,”

“That’s too bad Castiel. We’ll try again tomorrow.”

Heels on stone echoing away from him was the last thing Castiel heard before he was left alone again.


	13. Guilty Pleasures

**Summary for the Chapter:**

> Dean’s got plenty of guilty pleasures but his biggest has always been the plus size woman who he can make squirt all night long.

Dean has plenty of guilty pleasures. From TV shows and movies, to the occasional pop music he jams along to when Sam’s not in the car. He’s got a love for dogs that he’ll never admit to, and he hides the fact that he likes fresh fruit because he knows Sam will give him shit for it. But his biggest guilty pleasure had always been you, and the things he could do to your body that he’d never been able to find with anyone else.

You weren’t the average type Dean would bring home, at least not around Sam. Instead of long legs and a trim waist, you were soft and curvy with more than just a little fat around your middle. When he’d hit on you at the bar 3 year before, you’d scoffed at him, and asked how much his buddies were paying him to flirt with you. A gorgeous man like him would never hit on a woman as big as you.

But the answer was none and he was there alone, looking for someone to have a few drinks with, and maybe more if the night went well. And went well it did as he took you back to your place and showed you that your size only turned him on more.

He was all hands and mouth, stroking every inch of skin you possessed, and he laved his tongue over every dip and roll. You’d been with your fair share of men before, but never had one that worshipped your body like Dean did. He was insatiable, and when he learned he could make you cum like a fountain, he was even more hungry to wring every drop of pleasure from your curvaceous body.

He’d called that morning asking if you were free for the weekend. He was off for awhile and wanted to see you. You’d smirked into the phone, images of his long, firm body pressed against yours flew through your mind as you told him yes. He agreed to be by later that night, and like usual he showed up with a olive green duffle flung over his shoulder, his bright moss colored eyes shining as bright as his smile.

“How you doing sweetheart?’

“Better now that you’re here.”

He’d followed you inside, his duffle tossed haphazardly to your sofa as he encircled you in his strong arms, pulling you in till your breasts pressed against the flat expanse of his plaid and grey covered chest.

“God I missed this,” he rasped, his hands sliding down your back to the globes of your ass, squeezing gently as his plush lips landed on yours.

You groaned into the kiss, feeling his hands press you closer to him, his arousal evident already in the front of his jeans, pressing hard against your belly as his tongue licked into your mouth.

You let him taste you, his tongue dancing with yours as your hands ran up his chest and over his broad shoulders. The muscle underneath rolling and rippling with every squeeze of his hands on your backside.

As good as his kisses were you pulled away, your brain feeling dizzy already with desire.

His head fell to the crook of your neck, his luscious full lips finding your pulse point and sucking a dark purple bruise there quickly. Your fingers ran up to tug at the short hairs at the back of Dean’s head.

“Fuck, you taste good.” He growled as he licked up your neck to the spot just behind your ear. “Can’t wait to taste the rest of you.”

You let out a shuddered breath and stepped out of Dean’s embrace. “If you want to taste more of me, we should probably move this to my bedroom.”

Dean gave a sly smirk and walked around you to gesture down the hall for you to lead the way. “After you beautiful.”

You let out a soft giggle, still not used to a compliment like that, and strolled down the hall to your room.

The room was already ready for the two of you. A bottle of lube and a hand towel lay on your bedside table, several bath towels were already spread over the bed that was stripped down to just a simple sheet and a few pillows.

“You were prepared this time.” Dean removed his red and grey plaid shirt as you circled the bed.

“I learned my lesson from the last time you were here. And it’s a new mattress. I would rather not have to steam clean it after only a week and a half.” You watched Dean kick off his boots and shucking his jeans to the floor before stalking his way over to you.

“A week and a half huh? Guess we should break it in the right way.”

You gave a shriek of surprise as Dean grabbed you around your middle and pulled you sideways onto your bed, his tall frame stretching out over you as you settled onto your back, his mouth crashing against yours in a searing kiss.

His hands roamed over your frame, tangling in the hem of your t-shirt and dragging it up till he could cup the side of your covered breast, his thumb rubbing over the sensitive nub beneath your cotton bra feeling it hardened under his touch.

You moaned softly, arching into his caress as Dean’s lips mouthed over your jaw to your ear.

“Strip,” he rasped, his voice thick with arousal. Dean pulled away to sit back on his heels, and pulled his shirt over his head watching you as you stripped out of your shirt, bra, jeans, and underwear.

Naked before him, Dean couldn’t help letting his eyes rake over your body as you moved to lay back against your pillows. You thighs naturally closing as you settled against them, hiding the pussy he had been craving for almost a week.

He crawled over to you, his knees nudging you legs apart as he balances himself on his hands above you, each wide palm spread out next to your head on the pillow. Slowly he lowered himself, his weight pressing into you perfectly as his lips sought out yours; his covered cock rutting slowly against your already damp folds.

Peppered kisses over your jaw and throat had you writhing under him, and his breath was hot and raspy against your ear. “Don’t hide from me sweetheart. Been looking forward to seeing you for days. Been thinking about you and this body. So soft and warm.” His lips traveled down your body, caressing your collarbone before moving over your chest, his tongue flicking out to trace a lazy pattern to your right breast, licking a solid strip over the taut peak, and sending arousal straight to your core. “These tits, fuck, all I can think about is having them in my face. My mouth on them, how they feel squeezed around my cock.”

You threaded your fingers into his hair as Dean pulled your nipple into his mouth, sucking gently, and lapping at it with a hum of satisfaction. Mewls of pleasure left your lips as you panted, Dean’s teeth tugging slightly before letting the stiff nub go, licking and sucking at your soft skin untill he reached the other breast. A small mark on the inner side of your left breast bloomed as he teased the peak, his lips and tongue working at a maddening pace that had you thrusting your hips up towards his clothed erection.

“Dean,” you moaned and he smiled against your breast, his green eyes looking up at you through impossibly long, dark lashes.

“What is it sweetheart?” He worried your nipple between his teeth, pulling it slightly before letting it go again. “Need more?”

Your throat felt dry already and all you could manage was a frantic nod and a gasped, “Please.” as he licked down the slope of your breasts.

His rough, calloused hands came up to cover your chest as he crawled down your torso, his mouth finding every inch of skin it could. The tip of his tongue traced every stretch mark it came across, mapping out the expanse of your skin as his thumbs toyed with your nipples.

Sparks of pleasure shot down your spine and straight to your clit as Dean sucked a path down your stomach, his tongue dipping into your belly button making you arch your back up off the bed, breathy moans the only sounds you could manage as his hands skimmed down your frame to grip at your hips.

Dean kissed, sucked, and licked down your left thigh, his mouth finding a new place to lav attention to at every turn as he worked his way back up towards the apex of your thighs. He let only hot puffs of breath ghost over your mound, your hips canting towards his face as he skipped over it to give your right thigh the same treatment.

He bit gently at the flesh his mouth encountered, sucking till bruises appeared along your skin before licking wet trails up and down your thigh.

Each breath came out in pants, and you groaned out your need to feel more of Dean. To have his lips and tongue caress your sensitive folds, and his fingers delve deep and fondle the rough patch of nerves inside your pussy.

Feather light kisses rained over your already sodden pussy lips, and you felt like you might explode if Dean didn’t apply more pressure. A huff of air hit your damp skin making you jerk as he started to speak again.

“So fucking beautiful when you want me like this, pussy already wet and wanting.” He kissed your mound again, his nose nuzzling into you as he inhaled the scent of your arousal. “God you smell so good. Miss this.” His tongue swiped flat over your folds, a cry of pleasure at the contact leaving your throat as Dean groaned at the flavor coating his taste buds. “You taste so fucking good. Need you, need more.”

Dean’s mouth dove into you like a starving man, his tongue pushing between your folds as his hands moved down, his thumbs coming out to spread your lips open farther. The tip of his tongue ran a path from your clit down to your entrance, dipping in quick before running back up to circle and flick your swollen bundle of nerves.

It was like being hit with lightning as pleasure rocked through your body. Every lick, suck and kiss against your pussy drove you higher, a band of need tightening inside you as minutes passed under Dean’s ministrations.

Ever so slowly Dean moved his right hand down, his tongue pressing rapidly against your clit to distract you as he pressed a single digit inside your cunt. Your soft mewl at the added sensation gave Dean the go ahead he needed to insert a second, stretching and filling your channel as he started to work them in and out at a slower pace than his tongue was moving.

You knew what was coming next, knew at any moment he was going to crook his fingers, dragging them over your g-spot, building up the speed of his thrusts until you were coating him in your juices. The anticipation of it was almost as exhilarating as Dean’s actions themselves, and when he finally did crook them inside you, you let out a loud moan of his name, the word ‘Yes’ hissed between your teeth as he started picking up the pace.

His fingers raced along your inner walls, the rough bundle of nerves Dean’s main focus as he fingered you. He knew this was going to make you cum so hard that you would fill his palm with liquid, coating the lower half of his face.

Dean sucked your clit into his mouth, his tongue fervently moving over the nub as you rocked harshly down against his face and fingers, chasing the orgasm you knew was coming.

Like an overfilled water balloon, you felt yourself burst, a gush of your cum flowing out of you and all over Dean. His hand continued to hammer away inside of you making your juices splash up his forearm as obscene sucking sounds came from between your legs and you moaned out loudly in ecstasy.

As soon as Dean felt your walls stop fluttering he pulled his mouth away, your cum dripping from his chin as he gazed up at you. “Fuck, that was fucking amazing, and you fucking taste amazing.” He grunted low in his throat, rubbing his cock against the mattress as his thumb on his left hand stroked over your clit, making you whine. He sounded wrecked already, and you cried out in need when he muttered out a simple, “More.”

His tongue struck your over stimulated clit again, replacing his thumb, and this time his speed was nothing short of ravenous as he set to work again on making you squirt a second time. Pounding thrusts of his fingers in and out of your hole made you thrash about, a string of curses flowing from your lips as you felt another build of pressure in your pelvis. The sucking of your clit and vigorous thrusts of his fingers became too much, and with a shout you came a second time, cum splashing over Dean again, this time much quicker than the last.

“Jesus babe, that was fast.”

You panted, a single ’Fuck’ which was all you could manage as you lay twitching, your lower half soaked just as much as Dean was.

He pulled his fingers out and sat up, climbing off your bed backwards to pull his damp boxer briefs off his legs. He used them to dry his hand, arm, chest and face, his tongue licking his lips repeatedly as he moved around the bed to grab the lube off the bedside table.

You glanced over at Dean, watching him pour a dollop of slick on his fingers while strolling back towards the end of your bed.

“Oh fuck,” you groaned knowing he was going to try and make you cum again. “Dean,” you warned. Your body was telling you that it was too much, but you were still craving more.

“You put the lube out sweetheart. I know you want this.” He slipped his slicked up digits between your folds making you jerk as they ran over your swollen clit before he rubbed them down to your entrance. “All you gotta do is say the words and we stop, but I bet you still want more.” He pushed in just a little, the tips of his fingers pressing against your walls as he leaned down to kiss your knee, licking the bit of your cum he found there. “You want more?”

The deep rasp of Dean’s voice was almost enough to make you cum again, and you thrust yourself down on his fingers, feeling them slide in further only to have Dean pull them almost all the way out.

He clicked his tongue at you, “Gotta talk to me babe. Tell me what you want.” His fingers left your pussy to trail back up to your clit, pressing firm circles into it.

You moaned and rocked against Dean’s fingers. “Please Dean, I need more. Make me come one more time before you fuck me.”

Without warning Dean brought his fingers down and slammed them inside you, pistoning them against your walls, the crooked digits striking your g-spot with precision till you were arching up off the bed again.

The sounds you and your body were making were beyond your control, curses and Dean’s name a fixture in your vocabulary as you felt that familiar building again. The wet squelches sounding from your cunt with every push of Dean’s fingers would have made you blush had this been the first time you’d slept with him, but being that he’d fucked you more times than you can remember, you relished in it.

The slick of his lubed fingers made every stroke all too easy, and when that dam of pressure broke again he almost laughed at how fantastic it was that he could make you cum like that. He didn’t stop though, his fingers still working as he reached his left hand down between your legs as well to rub fiercely at your clit.

“How many has that been? Three. I think you can do better.”

You cursed, your body begging for everything to stop but also for him to keep going, the euphoria of a fourth orgasm peaking and washing over you; a generous amount of slick pouring from your body and soaking the towels underneath your quivering frame.

“There’s my girl,” he drawled as he moved on his knees to line himself up with your body. He withdrew his fingers and wrapped them around his engorged cock as he spread his pre-cum down his length along with your cum and the lube covering his hand.

He let himself go, reaching for your open thighs and pulling you down the mattress untill he could press himself into you, his thick cock stretching you open, and filling you completely.

Your pussy spasmed at the intrusion, still so sensitive from the four orgasms before, and when he drew back you shuddered before bracing yourself for the moment he slammed himself home again. The head of his cock hammered into your sweet spot, blinding flashes of white filled your vision and you clamped your eyes shut as you reached down to grip his wrists for support.

Dean dug his fingers into your fleshy thighs, watching your breasts bounce with every thrust of his pelvis into yours, the urge to have them in his mouth more than he could resist, and he bent forward, bracing his right hand next to you on the bed as he wrapped his lips around your left nipple.

He hitched your right leg up over his hip, his strokes deeper, harder, and quicker making your toes curl and foot arch along his backside.

Your hands clawed for purchase on his biceps and back, your right hand tugging and guiding his mouth to show your right breast just as much affection as your left. A keen of pleasure rattled through you as he nipped at your flesh, his lips letting go to crash against your mouth, his tongue pushing past your swollen lips to tangle with yours.

Sweat mixed with your juices had you sliding easily against each other, Dean’s pelvis crashing against yours, rubbing deliriously good over your clit as he stroked his length in and out of your pussy. There was almost no warning this time as you came a fifth time, this one just as intense as the last and lasted longer as he kept fucking himself into you.

“Jesus, Y/N,” he growed, his cock pulsating and unloading inside you as your pussy clenched, your cum washing over his length, down his sac, and coating his thighs. Dean buried his face in your neck, his lips sucking at your skin as your pussy continued to spasm around him, his rocking hips pulling a smaller yet equally intense sixth orgasm from you before you finally relaxed underneath him.

Dean removed his soaked and softening length from your body, aftershocks of pleasure making your body twitch as he flopped onto his back next to you.

“Holy shit that was fucking awesome. How many was that? Five?”

“Six,” you panted harshly. Your toes still curled and thighs shook as the moisture on them cooled.

“Six. Shit no wonder you’re still twitching over there.” Dean rolled onto his side, propping himself up on his elbow. “You okay? I didn’t hurt you did I?”

You laid there taking a moment to mentally check over your body. “No, not really. I’ll be sore later, but it was worth it. Can’t really feel my legs though, and I’m pretty sure my toes are still curled.”

Dean glanced down and laughed. “That they are sweetheart.” He moved his hand to push some of the hair stuck to the sweat along your forehead out of the way before leaning down to kiss you. “That was just what I needed, and when you regain some feeling in your lower half I’ll help clean you up in the shower.”

You hummed, leaning your head up to press another kiss to his sinful pink lips. “Sounds good to me. I still have that strawberries and cream body wash you like to use under the sink. I know it’s one of your guilty pleasures.”

“It’s ain’t the only one sweetheart, and I think out of all of the ones I have you are my biggest. You, your body, and how hard you make me with just a simple sway of your hips.” Dean pressed himself into your side, his cock already starting to swell again as he ran his hand over the curves of your body.


	14. Bats and Ms. Quinn

**Summary for the Chapter:**

> Aesthetic for Role Playing with Dean

The great thing about your relationship with Dean was you both loved the DC universe, his love of the Dark Knight making you laugh since you had always had a soft spot for the villains; Harley Quinn always being your favorite. This year for Halloween instead of just sitting around, watching horror movies and gorging on candy, you decided to dress up as your favorite hero and villain.

“Come on Bats, show me whatcha got?” You teased as Dean pressed his hard chest plate into your leather covered back, your hands pulled back behind you as he rested the cool metal of a set of cuffs at your wrist..

“You’ve been a very bad girl Ms.Quinn. I think it’s time for a little punishment.” The low gravel of his voice shot heat straight down to your clit, desire pooling in your belly.

“Bring it on Batsy.”


	15. Best Case Scenario

**Summary for the Chapter:**

> Aesthetic with Dean for the square Gangbang

When Dean Winchester decided he needed to check out the parties that their male victims had been disappearing from, he had no idea just what kind of party he was about to attend, and participate in.


	16. A Blizzard at Midnight

**Summary for the Chapter:**

> Aesthetic with Sam for the square food play

Inspired by a fic no longer on tumblr.


	17. All Coming Back to Me Now

**Summary for the Chapter:**

> Aesthetic for my DeanJo Chestervelle square

_But when you touch me like this / And you hold me like that_  
I just have to admit / That it’s all coming back to me  
When I touch you like this / And I hold you like that  
It’s so hard to believe but / It’s all coming back to me  
(It’s all coming back, it’s all coming back to me now)

 _There were moments of gold / And there were flashes of light_  
There were things I’d never do again / But then they’d always seemed right  
There were nights of endless pleasure / It was more than any laws allow  
Baby Baby

 _If I kiss you like this / And if you whisper like that_  
It was lost long ago / But it’s all coming back to me  
If you want me like this / And if you need me like that  
It was dead long ago / But it’s all coming back to me  
It’s so hard to resist / And it’s all coming back to me  
I can barely recall / But it’s all coming back to me now

_[All Coming Back to Me Now by Celine Dion](https://t.umblr.com/redirect?z=https%3A%2F%2Fwww.youtube.com%2Fwatch%3Fv%3DpDxoj-tDDIU&t=YzY2OWEyNmNiODljMTRkOTBmZTMyYjU4YWU5ZWQwMGJjNDdkNWU2MSxMQ2pCeFhPWg%3D%3D&b=t%3A-k5u1SKdx4Vfi1qg3DHxWA&p=https%3A%2F%2Fleatherwhiskeycoffeeplaid.tumblr.com%2Fpost%2F149549471241%2Ftitle-all-coming-back-to-me-now-square-filled&m=1) _


	18. Burning the Midnight Oil

**Summary for the Chapter:**

> Aesthetic of a Sam Wesson x Reader x Dean Smith for my office sex square

When your boss Dean Smith said he was staying late with Sam Wesson from tech support and they would need you to stay behind as well, you had no idea that this was what they had in mind.


	19. Yes, Sir

**Summary for the Chapter:**

> Aesthetic with Sam for bondage square

Sam likes to always be in control. His passion for bondage and being the dominate over a submissive woman is his greatest sexual desire


	20. Go All Night

**Summary for the Chapter:**

> DeanDonna aesthetic for the square cock rings

Dean couldn’t get enough of Donna and with just one simple metal ring, tight around his cock and balls, he could go all night with her.


	21. Our Submissive

**Summary for the Chapter:**

> Dean x Reader x Sam aesthetic for dom/sub square

Finally Sam and Dean have a submissive they can dominate together.


	22. Lips Built for Sin

**Summary for the Chapter:**

> Oral fixation aesthetic with Dean

Dean Winchester’s sinfully full luscious lips are built to be worshiped especially as they worship a woman’s body.


	23. Secrets in Lace

**Summary for the Chapter:**

> A BelaSam aesthetic

The things Sam and Bela do in the dark are just secrets full of lace and debauchery.


End file.
